From aa4372c35bd7e481eab7d4d843a4629874a43092 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Wed, 11 Mar 2026 11:29:29 +0100
Subject: [PATCH 01/33] Add sessions commands

---
 apps/cli/commands/ai.ts | 38 +++++++++++++++++++++++++++++++++++---
 1 file changed, 35 insertions(+), 3 deletions(-)

diff --git a/apps/cli/commands/ai.ts b/apps/cli/commands/ai.ts
index c2479a8f3c..7cc39ceac7 100644
--- a/apps/cli/commands/ai.ts
+++ b/apps/cli/commands/ai.ts
@@ -308,9 +308,41 @@ export const registerCommand = ( yargs: StudioArgv ) => {
 		command: 'ai',
 		describe: __( 'AI-powered WordPress assistant' ),
 		builder: ( yargs ) => {
-			return yargs.option( 'path', {
-				hidden: true,
-			} );
+			return yargs
+				.option( 'path', {
+					hidden: true,
+				} )
+				.command( {
+					command: 'sessions',
+					describe: __( 'Manage AI sessions' ),
+					builder: ( sessionsYargs ) => {
+						return sessionsYargs
+							.command( {
+								command: 'list',
+								describe: __( 'List AI sessions' ),
+								handler: async () => {
+									// Not implemented
+								},
+							} )
+							.command( {
+								command: 'resume <id>',
+								describe: __( 'Resume an AI session' ),
+								handler: async () => {
+									// Not implemented
+								},
+							} )
+							.command( {
+								command: 'delete <id>',
+								describe: __( 'Delete an AI session' ),
+								handler: async () => {
+									// Not implemented
+								},
+							} )
+							.version( false )
+							.demandCommand( 1, __( 'You must provide a valid ai sessions command' ) );
+					},
+					handler: async () => {},
+				} );
 		},
 		handler: async () => {
 			try {

From 880e56e7eea23e7d074027d31258733a4280dedf Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Wed, 11 Mar 2026 12:46:36 +0100
Subject: [PATCH 02/33] Persist AI sessions as JSONL in date-based appdata
 subfolders

---
 apps/cli/ai/ui.ts                      |   2 +-
 apps/cli/commands/ai.ts                | 203 ++++++++++++++++++++--
 apps/cli/lib/ai-sessions.ts            | 223 +++++++++++++++++++++++++
 apps/cli/lib/tests/ai-sessions.test.ts | 122 ++++++++++++++
 4 files changed, 537 insertions(+), 13 deletions(-)
 create mode 100644 apps/cli/lib/ai-sessions.ts
 create mode 100644 apps/cli/lib/tests/ai-sessions.test.ts

diff --git a/apps/cli/ai/ui.ts b/apps/cli/ai/ui.ts
index 08e513c0cb..188df91224 100644
--- a/apps/cli/ai/ui.ts
+++ b/apps/cli/ai/ui.ts
@@ -246,7 +246,7 @@ const toolDisplayNames: Record< string, string > = {
 	TodoWrite: 'Update todo list',
 };
 
-function getToolDetail( name: string, input: Record< string, unknown > ): string {
+export function getToolDetail( name: string, input: Record< string, unknown > ): string {
 	switch ( name ) {
 		case 'mcp__studio__site_create':
 			return typeof input.name === 'string' ? input.name : '';
diff --git a/apps/cli/commands/ai.ts b/apps/cli/commands/ai.ts
index 7cc39ceac7..231b1e7793 100644
--- a/apps/cli/commands/ai.ts
+++ b/apps/cli/commands/ai.ts
@@ -25,6 +25,7 @@ import { runCommand as runLogoutCommand } from 'cli/commands/auth/logout';
 import { getAnthropicApiKey, getAuthToken } from 'cli/lib/appdata';
 import { Logger, LoggerError, setProgressCallback } from 'cli/logger';
 import { StudioArgv } from 'cli/types';
+import type { SDKMessage } from '@anthropic-ai/claude-agent-sdk';
 
 const logger = new Logger< string >();
 
@@ -35,6 +36,129 @@ function isPromptAbortError( error: unknown ): boolean {
 	);
 }
 
+function getErrorMessage( error: unknown ): string {
+	if ( error instanceof Error ) {
+		return error.message;
+	}
+
+	return String( error );
+}
+
+function extractAssistantMessageBlocks( message: SDKMessage ): AssistantMessageBlock[] {
+	if ( message.type !== 'assistant' ) {
+		return [];
+	}
+
+	const blocks: AssistantMessageBlock[] = [];
+	for ( const block of message.message.content ) {
+		if ( block.type === 'text' && block.text ) {
+			blocks.push( {
+				type: 'text',
+				text: block.text,
+			} );
+		}
+
+		if ( block.type === 'tool_use' && block.name ) {
+			const detail =
+				block.input && typeof block.input === 'object'
+					? getToolDetail( block.name, block.input as Record< string, unknown > )
+					: '';
+			blocks.push( {
+				type: 'tool_use',
+				name: block.name,
+				detail: detail || undefined,
+			} );
+		}
+	}
+
+	return blocks;
+}
+
+function toToolResultText( value: unknown ): string {
+	if ( Array.isArray( value ) ) {
+		const lines = value
+			.map( ( item ) => {
+				if ( typeof item === 'string' ) {
+					return item;
+				}
+
+				if ( item && typeof item === 'object' ) {
+					const typedItem = item as { type?: unknown; text?: unknown };
+					if ( typedItem.type === 'text' && typeof typedItem.text === 'string' ) {
+						return typedItem.text;
+					}
+
+					try {
+						return JSON.stringify( item, null, 2 );
+					} catch {
+						return String( item );
+					}
+				}
+
+				return String( item );
+			} )
+			.map( ( line ) => line.trim() )
+			.filter( ( line ) => line.length > 0 );
+
+		return lines.join( '\n' );
+	}
+
+	if ( typeof value === 'string' ) {
+		return value.trim();
+	}
+
+	if ( value === null || value === undefined ) {
+		return '';
+	}
+
+	try {
+		return JSON.stringify( value, null, 2 );
+	} catch {
+		return String( value );
+	}
+}
+
+function extractToolResult( message: SDKMessage ): { ok: boolean; text: string } | undefined {
+	if ( message.type !== 'user' ) {
+		return undefined;
+	}
+
+	const rawResult = message.tool_use_result;
+	if ( ! rawResult ) {
+		return undefined;
+	}
+
+	if ( typeof rawResult !== 'object' ) {
+		const text = String( rawResult ).trim();
+		return {
+			ok: true,
+			text: text || 'Tool completed with no textual output.',
+		};
+	}
+
+	const typedResult = rawResult as {
+		content?: unknown;
+		isError?: unknown;
+		is_error?: unknown;
+	};
+	const isError = typedResult.isError === true || typedResult.is_error === true;
+	const textFromContent = toToolResultText( typedResult.content );
+
+	if ( textFromContent ) {
+		return {
+			ok: ! isError,
+			text: textFromContent,
+		};
+	}
+
+	return {
+		ok: ! isError,
+		text: isError
+			? 'Tool returned an error with no textual output.'
+			: 'Tool completed with no textual output.',
+	};
+}
+
 export async function runCommand(): Promise< void > {
 	const ui = new AiChatUI();
 	let currentProvider: AiProviderId = await resolveInitialAiProvider();
@@ -43,6 +167,31 @@ export async function runCommand(): Promise< void > {
 	ui.start();
 	ui.showWelcome();
 
+	let sessionRecorder: AiSessionRecorder | undefined;
+	let didDisableSessionPersistence = false;
+	try {
+		sessionRecorder = await AiSessionRecorder.create();
+	} catch ( error ) {
+		didDisableSessionPersistence = true;
+		ui.showError( `Session persistence disabled: ${ getErrorMessage( error ) }` );
+	}
+
+	const persist = async ( callback: ( recorder: AiSessionRecorder ) => Promise< void > ) => {
+		if ( ! sessionRecorder ) {
+			return;
+		}
+
+		try {
+			await callback( sessionRecorder );
+		} catch ( error ) {
+			sessionRecorder = undefined;
+			if ( ! didDisableSessionPersistence ) {
+				didDisableSessionPersistence = true;
+				ui.showError( `Session persistence disabled: ${ getErrorMessage( error ) }` );
+			}
+		}
+	};
+
 	let sessionId: string | undefined;
 	let currentModel: AiModelId = DEFAULT_MODEL;
 
@@ -126,12 +275,20 @@ export async function runCommand(): Promise< void > {
 			}]\n\n${ prompt }`;
 		}
 
+		await persist( ( recorder ) =>
+			recorder.recordUserMessage( {
+				text: prompt,
+				source: 'prompt',
+				sitePath: site?.path,
+			} )
+		);
+
 		const agentQuery = startAiAgent( {
 			prompt: enrichedPrompt,
 			env,
 			model: currentModel,
 			resume: sessionId,
-			onAskUser: ( questions ) => ui.askUser( questions ),
+			onAskUser: ( questions ) => askUserAndPersistAnswers( questions ),
 		} );
 
 		ui.onInterrupt = () => {
@@ -139,22 +296,44 @@ export async function runCommand(): Promise< void > {
 		};
 
 		let maxTurnsResult: { numTurns: number; costUsd: number } | undefined;
+		let turnStatus: TurnStatus = 'interrupted';
 
-		for await ( const message of agentQuery ) {
-			const result = ui.handleMessage( message );
-			if ( result ) {
-				sessionId = result.sessionId;
-				if ( 'maxTurnsReached' in result && result.maxTurnsReached ) {
-					maxTurnsResult = {
-						numTurns: result.numTurns,
-						costUsd: result.costUsd,
-					};
+		try {
+			for await ( const message of agentQuery ) {
+				const assistantBlocks = extractAssistantMessageBlocks( message );
+				if ( assistantBlocks.length > 0 ) {
+					await persist( ( recorder ) => recorder.recordAssistantMessage( assistantBlocks ) );
+				}
+
+				const toolResult = extractToolResult( message );
+				if ( toolResult ) {
+					await persist( ( recorder ) => recorder.recordToolResult( toolResult ) );
+				}
+
+				const result = ui.handleMessage( message );
+				if ( result ) {
+					sessionId = result.sessionId;
+					await persist( ( recorder ) => recorder.recordAgentSessionId( result.sessionId ) );
+
+					if ( 'maxTurnsReached' in result && result.maxTurnsReached ) {
+						maxTurnsResult = {
+							numTurns: result.numTurns,
+							costUsd: result.costUsd,
+						};
+						turnStatus = 'max_turns';
+					} else {
+						turnStatus = result.success ? 'success' : 'error';
+					}
 				}
 			}
+		} catch ( error ) {
+			turnStatus = 'error';
+			throw error;
+		} finally {
+			await persist( ( recorder ) => recorder.recordTurnClosed( turnStatus ) );
+			ui.endAgentTurn();
 		}
 
-		ui.endAgentTurn();
-
 		if ( maxTurnsResult ) {
 			ui.showInfo(
 				`Used ${ maxTurnsResult.numTurns } turns · $${ maxTurnsResult.costUsd.toFixed( 4 ) }`
diff --git a/apps/cli/lib/ai-sessions.ts b/apps/cli/lib/ai-sessions.ts
new file mode 100644
index 0000000000..e4de40ac0a
--- /dev/null
+++ b/apps/cli/lib/ai-sessions.ts
@@ -0,0 +1,223 @@
+import crypto from 'crypto';
+import fs from 'fs/promises';
+import path from 'path';
+import { getAppdataDirectory } from 'cli/lib/appdata';
+
+export type TurnStatus = 'success' | 'error' | 'max_turns' | 'interrupted';
+
+export type AssistantMessageBlock =
+	| {
+			type: 'text';
+			text: string;
+	  }
+	| {
+			type: 'tool_use';
+			name: string;
+			detail?: string;
+	  };
+
+export type AiSessionEvent =
+	| {
+			type: 'session.started';
+			timestamp: string;
+			version: 1;
+			sessionId: string;
+	  }
+	| {
+			type: 'session.linked';
+			timestamp: string;
+			agentSessionId: string;
+	  }
+	| {
+			type: 'site.selected';
+			timestamp: string;
+			siteName: string;
+			sitePath: string;
+	  }
+	| {
+			type: 'user.message';
+			timestamp: string;
+			text: string;
+			source: 'prompt' | 'ask_user';
+			sitePath?: string;
+	  }
+	| {
+			type: 'assistant.message';
+			timestamp: string;
+			blocks: AssistantMessageBlock[];
+	  }
+	| {
+			type: 'tool.result';
+			timestamp: string;
+			ok: boolean;
+			text: string;
+	  }
+	| {
+			type: 'agent.question';
+			timestamp: string;
+			question: string;
+			options: Array< {
+				label: string;
+				description: string;
+			} >;
+	  }
+	| {
+			type: 'turn.closed';
+			timestamp: string;
+			status: TurnStatus;
+	  };
+
+export function getAiSessionsRootDirectory(): string {
+	return path.join( getAppdataDirectory(), 'sessions' );
+}
+
+function formatDatePart( value: number ): string {
+	return String( value ).padStart( 2, '0' );
+}
+
+export function getAiSessionsDirectoryForDate( date: Date ): string {
+	const year = String( date.getFullYear() );
+	const month = formatDatePart( date.getMonth() + 1 );
+	const day = formatDatePart( date.getDate() );
+	return path.join( getAiSessionsRootDirectory(), year, month, day );
+}
+
+function toIsoTimestamp( value?: Date ): string {
+	return ( value ?? new Date() ).toISOString();
+}
+
+export class AiSessionRecorder {
+	public readonly sessionId: string;
+	public readonly filePath: string;
+
+	private linkedAgentSessionIds = new Set< string >();
+
+	private constructor( sessionId: string, filePath: string ) {
+		this.sessionId = sessionId;
+		this.filePath = filePath;
+	}
+
+	static async create( options: { startedAt?: Date } = {} ): Promise< AiSessionRecorder > {
+		const startedAt = options.startedAt ?? new Date();
+		const sessionId = crypto.randomUUID();
+		const directory = getAiSessionsDirectoryForDate( startedAt );
+		const filePath = path.join( directory, `${ sessionId }.jsonl` );
+
+		await fs.mkdir( directory, { recursive: true } );
+
+		const recorder = new AiSessionRecorder( sessionId, filePath );
+		await recorder.appendEvent( {
+			type: 'session.started',
+			timestamp: toIsoTimestamp( startedAt ),
+			version: 1,
+			sessionId,
+		} );
+
+		return recorder;
+	}
+
+	async recordAgentSessionId( agentSessionId: string ): Promise< void > {
+		if ( this.linkedAgentSessionIds.has( agentSessionId ) ) {
+			return;
+		}
+
+		this.linkedAgentSessionIds.add( agentSessionId );
+		await this.appendEvent( {
+			type: 'session.linked',
+			timestamp: toIsoTimestamp(),
+			agentSessionId,
+		} );
+	}
+
+	async recordSiteSelected( site: { name: string; path: string } ): Promise< void > {
+		await this.appendEvent( {
+			type: 'site.selected',
+			timestamp: toIsoTimestamp(),
+			siteName: site.name,
+			sitePath: site.path,
+		} );
+	}
+
+	async recordUserMessage( options: {
+		text: string;
+		source: 'prompt' | 'ask_user';
+		sitePath?: string;
+	} ): Promise< void > {
+		await this.appendEvent( {
+			type: 'user.message',
+			timestamp: toIsoTimestamp(),
+			text: options.text,
+			source: options.source,
+			sitePath: options.sitePath,
+		} );
+	}
+
+	async recordAssistantMessage( blocks: AssistantMessageBlock[] ): Promise< void > {
+		if ( blocks.length === 0 ) {
+			return;
+		}
+
+		await this.appendEvent( {
+			type: 'assistant.message',
+			timestamp: toIsoTimestamp(),
+			blocks,
+		} );
+	}
+
+	async recordToolResult( options: { ok: boolean; text: string } ): Promise< void > {
+		await this.appendEvent( {
+			type: 'tool.result',
+			timestamp: toIsoTimestamp(),
+			ok: options.ok,
+			text: options.text,
+		} );
+	}
+
+	async recordAgentQuestion( options: {
+		question: string;
+		options: Array< {
+			label: string;
+			description: string;
+		} >;
+	} ): Promise< void > {
+		await this.appendEvent( {
+			type: 'agent.question',
+			timestamp: toIsoTimestamp(),
+			question: options.question,
+			options: options.options,
+		} );
+	}
+
+	async recordTurnClosed( status: TurnStatus ): Promise< void > {
+		await this.appendEvent( {
+			type: 'turn.closed',
+			timestamp: toIsoTimestamp(),
+			status,
+		} );
+	}
+
+	private async appendEvent( event: AiSessionEvent ): Promise< void > {
+		await fs.appendFile( this.filePath, `${ JSON.stringify( event ) }\n`, {
+			encoding: 'utf8',
+		} );
+	}
+}
+
+export async function readAiSessionEventsFromFile( filePath: string ): Promise< AiSessionEvent[] > {
+	const content = await fs.readFile( filePath, 'utf8' );
+	const lines = content
+		.split( '\n' )
+		.map( ( line ) => line.trim() )
+		.filter( ( line ) => line.length > 0 );
+	const events: AiSessionEvent[] = [];
+
+	for ( const line of lines ) {
+		try {
+			events.push( JSON.parse( line ) as AiSessionEvent );
+		} catch {
+			// Ignore malformed lines and keep loading the rest.
+		}
+	}
+
+	return events;
+}
diff --git a/apps/cli/lib/tests/ai-sessions.test.ts b/apps/cli/lib/tests/ai-sessions.test.ts
new file mode 100644
index 0000000000..26f963954c
--- /dev/null
+++ b/apps/cli/lib/tests/ai-sessions.test.ts
@@ -0,0 +1,122 @@
+import fs from 'fs/promises';
+import os from 'os';
+import path from 'path';
+import { afterEach, describe, expect, it } from 'vitest';
+import {
+	AiSessionRecorder,
+	getAiSessionsDirectoryForDate,
+	readAiSessionEventsFromFile,
+} from 'cli/lib/ai-sessions';
+
+describe( 'ai-sessions', () => {
+	let testRoot: string | undefined;
+
+	afterEach( async () => {
+		delete process.env.E2E;
+		delete process.env.E2E_APP_DATA_PATH;
+
+		if ( testRoot ) {
+			await fs.rm( testRoot, { recursive: true, force: true } );
+			testRoot = undefined;
+		}
+	} );
+
+	it( 'stores minimal conversation events as jsonl with explicit timestamp fields', async () => {
+		testRoot = await fs.mkdtemp( path.join( os.tmpdir(), 'studio-ai-sessions-' ) );
+		process.env.E2E = '1';
+		process.env.E2E_APP_DATA_PATH = testRoot;
+
+		const startedAt = new Date( '2026-03-11T10:00:00.000Z' );
+		const recorder = await AiSessionRecorder.create( { startedAt } );
+
+		await recorder.recordSiteSelected( {
+			name: 'My WordPress Website',
+			path: '/tmp/my-wordpress-website',
+		} );
+		await recorder.recordUserMessage( {
+			text: 'Help me create a plugin',
+			source: 'prompt',
+			sitePath: '/tmp/my-wordpress-website',
+		} );
+		await recorder.recordAssistantMessage( [
+			{ type: 'text', text: 'Sure, I can help with that.' },
+			{ type: 'tool_use', name: 'Read' },
+		] );
+		await recorder.recordToolResult( {
+			ok: true,
+			text: 'File read successfully',
+		} );
+		await recorder.recordAgentQuestion( {
+			question: 'Choose a plugin slug',
+			options: [
+				{
+					label: 'my-plugin',
+					description: 'Use default slug',
+				},
+			],
+		} );
+		await recorder.recordUserMessage( {
+			text: 'my-plugin',
+			source: 'ask_user',
+		} );
+		await recorder.recordAgentSessionId( 'agent-session-1' );
+		await recorder.recordTurnClosed( 'success' );
+
+		const events = await readAiSessionEventsFromFile( recorder.filePath );
+		expect( recorder.filePath.startsWith( getAiSessionsDirectoryForDate( startedAt ) ) ).toBe(
+			true
+		);
+		expect( events[ 0 ] ).toMatchObject( {
+			type: 'session.started',
+			version: 1,
+			sessionId: recorder.sessionId,
+			timestamp: startedAt.toISOString(),
+		} );
+		expect( events.find( ( event ) => event.type === 'user.message' ) ).toMatchObject( {
+			type: 'user.message',
+			source: 'prompt',
+			text: 'Help me create a plugin',
+		} );
+		expect( events.find( ( event ) => event.type === 'assistant.message' ) ).toMatchObject( {
+			type: 'assistant.message',
+			blocks: [
+				{ type: 'text', text: 'Sure, I can help with that.' },
+				{ type: 'tool_use', name: 'Read' },
+			],
+		} );
+		expect( events.find( ( event ) => event.type === 'turn.closed' ) ).toMatchObject( {
+			type: 'turn.closed',
+			status: 'success',
+		} );
+
+		const hasShortTimestampKey = events.some(
+			( event ) => typeof event === 'object' && event && 't' in event
+		);
+		expect( hasShortTimestampKey ).toBe( false );
+	} );
+
+	it( 'deduplicates linked agent session ids', async () => {
+		testRoot = await fs.mkdtemp( path.join( os.tmpdir(), 'studio-ai-sessions-' ) );
+		process.env.E2E = '1';
+		process.env.E2E_APP_DATA_PATH = testRoot;
+
+		const recorder = await AiSessionRecorder.create();
+		await recorder.recordAgentSessionId( 'agent-session-1' );
+		await recorder.recordAgentSessionId( 'agent-session-1' );
+		await recorder.recordAgentSessionId( 'agent-session-2' );
+
+		const events = await readAiSessionEventsFromFile( recorder.filePath );
+		const linkedEvents = events.filter( ( event ) => event.type === 'session.linked' );
+		expect( linkedEvents ).toHaveLength( 2 );
+		expect( linkedEvents ).toMatchObject( [
+			{
+				type: 'session.linked',
+				agentSessionId: 'agent-session-1',
+			},
+			{
+				type: 'session.linked',
+				agentSessionId: 'agent-session-2',
+			},
+		] );
+	} );
+} );

From b2f5ef4b86ca1b4a67106aa92bd0c9a8a1b73018 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Wed, 11 Mar 2026 14:35:36 +0100
Subject: [PATCH 03/33] Add sessions resuming capability

---
 apps/cli/ai/ui.ts                      |   8 +-
 apps/cli/commands/ai.ts                |  29 ++++-
 apps/cli/lib/ai-sessions.ts            | 154 ++++++++++++++++++++++++-
 apps/cli/lib/tests/ai-sessions.test.ts |  58 ++++++++++
 4 files changed, 242 insertions(+), 7 deletions(-)

diff --git a/apps/cli/ai/ui.ts b/apps/cli/ai/ui.ts
index 188df91224..5813fe87d4 100644
--- a/apps/cli/ai/ui.ts
+++ b/apps/cli/ai/ui.ts
@@ -291,7 +291,7 @@ export function getToolDetail( name: string, input: Record< string, unknown > ):
 		case 'Glob':
 			return typeof input.pattern === 'string' ? input.pattern : '';
 		default:
-			return '';
+			return typeof input.detail === 'string' ? input.detail : '';
 	}
 }
 
@@ -542,6 +542,10 @@ export class AiChatUI {
 		return this._activeSite;
 	}
 
+	set onSiteSelected( fn: ( ( site: SiteInfo ) => void ) | null ) {
+		this.siteSelectedCallback = fn;
+	}
+
 	constructor() {
 		const terminal = new ProcessTerminal();
 		this.tui = new TUI( terminal );
@@ -1790,7 +1794,7 @@ export class AiChatUI {
 				}
 				// Always show the loader after processing — the agent turn is still active
 				// and more messages are coming (next API call, tool execution, etc.)
-				if ( ! this.loaderVisible ) {
+				if ( ! this.replayMode && ! this.loaderVisible ) {
 					this.showLoader( this.randomThinkingMessage() );
 				}
 				return undefined;
diff --git a/apps/cli/commands/ai.ts b/apps/cli/commands/ai.ts
index 231b1e7793..084fabface 100644
--- a/apps/cli/commands/ai.ts
+++ b/apps/cli/commands/ai.ts
@@ -169,8 +169,18 @@ export async function runCommand(): Promise< void > {
 
 	let sessionRecorder: AiSessionRecorder | undefined;
 	let didDisableSessionPersistence = false;
+	let sessionId: string | undefined = options.resumeSession?.summary.agentSessionId;
+
 	try {
-		sessionRecorder = await AiSessionRecorder.create();
+		if ( options.resumeSession ) {
+			sessionRecorder = await AiSessionRecorder.open( {
+				sessionId: options.resumeSession.summary.id,
+				filePath: options.resumeSession.summary.filePath,
+				linkedAgentSessionIds: options.resumeSession.summary.linkedAgentSessionIds,
+			} );
+		} else {
+			sessionRecorder = await AiSessionRecorder.create();
+		}
 	} catch ( error ) {
 		didDisableSessionPersistence = true;
 		ui.showError( `Session persistence disabled: ${ getErrorMessage( error ) }` );
@@ -192,7 +202,6 @@ export async function runCommand(): Promise< void > {
 		}
 	};
 
-	let sessionId: string | undefined;
 	let currentModel: AiModelId = DEFAULT_MODEL;
 
 	async function prepareProviderSelection(
@@ -506,8 +515,20 @@ export const registerCommand = ( yargs: StudioArgv ) => {
 							.command( {
 								command: 'resume <id>',
 								describe: __( 'Resume an AI session' ),
-								handler: async () => {
-									// Not implemented
+								handler: async ( argv ) => {
+									try {
+										await runResumeSessionCommand( argv.id as string );
+									} catch ( error ) {
+										if ( error instanceof LoggerError ) {
+											logger.reportError( error );
+										} else {
+											const loggerError = new LoggerError(
+												__( 'Failed to resume AI session' ),
+												error
+											);
+											logger.reportError( loggerError );
+										}
+									}
 								},
 							} )
 							.command( {
diff --git a/apps/cli/lib/ai-sessions.ts b/apps/cli/lib/ai-sessions.ts
index e4de40ac0a..61ab86f8a7 100644
--- a/apps/cli/lib/ai-sessions.ts
+++ b/apps/cli/lib/ai-sessions.ts
@@ -67,6 +67,20 @@ export type AiSessionEvent =
 			status: TurnStatus;
 	  };
 
+export interface AiSessionSummary {
+	id: string;
+	filePath: string;
+	createdAt: string;
+	updatedAt: string;
+	agentSessionId?: string;
+	linkedAgentSessionIds: string[];
+}
+
+export interface LoadedAiSession {
+	summary: AiSessionSummary;
+	events: AiSessionEvent[];
+}
+
 export function getAiSessionsRootDirectory(): string {
 	return path.join( getAppdataDirectory(), 'sessions' );
 }
@@ -92,9 +106,10 @@ export class AiSessionRecorder {
 
 	private linkedAgentSessionIds = new Set< string >();
 
-	private constructor( sessionId: string, filePath: string ) {
+	private constructor( sessionId: string, filePath: string, linkedAgentSessionIds: string[] = [] ) {
 		this.sessionId = sessionId;
 		this.filePath = filePath;
+		this.linkedAgentSessionIds = new Set( linkedAgentSessionIds );
 	}
 
 	static async create( options: { startedAt?: Date } = {} ): Promise< AiSessionRecorder > {
@@ -116,6 +131,19 @@ export class AiSessionRecorder {
 		return recorder;
 	}
 
+	static async open( options: {
+		sessionId: string;
+		filePath: string;
+		linkedAgentSessionIds?: string[];
+	} ): Promise< AiSessionRecorder > {
+		await fs.access( options.filePath );
+		return new AiSessionRecorder(
+			options.sessionId,
+			options.filePath,
+			options.linkedAgentSessionIds ?? []
+		);
+	}
+
 	async recordAgentSessionId( agentSessionId: string ): Promise< void > {
 		if ( this.linkedAgentSessionIds.has( agentSessionId ) ) {
 			return;
@@ -221,3 +249,127 @@ export async function readAiSessionEventsFromFile( filePath: string ): Promise<
 
 	return events;
 }
+
+function getSessionIdFromPath( filePath: string ): string {
+	return path.basename( filePath, '.jsonl' );
+}
+
+async function listSessionFilesRecursively( directory: string ): Promise< string[] > {
+	try {
+		const entries = await fs.readdir( directory, { withFileTypes: true, encoding: 'utf8' } );
+
+		const nestedFiles = await Promise.all(
+			entries.map( async ( entry ) => {
+				const fullPath = path.join( directory, entry.name );
+
+				if ( entry.isDirectory() ) {
+					return listSessionFilesRecursively( fullPath );
+				}
+
+				if ( entry.isFile() && entry.name.endsWith( '.jsonl' ) ) {
+					return [ fullPath ];
+				}
+
+				return [];
+			} )
+		);
+
+		return nestedFiles.flat();
+	} catch ( error ) {
+		const fsError = error as NodeJS.ErrnoException;
+		if ( fsError.code === 'ENOENT' ) {
+			return [];
+		}
+
+		throw error;
+	}
+}
+
+async function readAiSessionSummaryFromFile(
+	filePath: string
+): Promise< AiSessionSummary | undefined > {
+	const events = await readAiSessionEventsFromFile( filePath );
+	if ( events.length === 0 ) {
+		return undefined;
+	}
+
+	const linkedAgentSessionIds: string[] = [];
+	let createdAt: string | undefined;
+	let updatedAt: string | undefined;
+	let sessionId = getSessionIdFromPath( filePath );
+
+	for ( const event of events ) {
+		updatedAt = event.timestamp;
+
+		if ( event.type === 'session.started' ) {
+			createdAt = event.timestamp;
+			if ( event.sessionId.trim().length > 0 ) {
+				sessionId = event.sessionId;
+			}
+		}
+
+		if (
+			event.type === 'session.linked' &&
+			! linkedAgentSessionIds.includes( event.agentSessionId )
+		) {
+			linkedAgentSessionIds.push( event.agentSessionId );
+		}
+	}
+
+	const stats = await fs.stat( filePath );
+	const fallbackTimestamp = stats.mtime.toISOString();
+
+	return {
+		id: sessionId,
+		filePath,
+		createdAt: createdAt ?? fallbackTimestamp,
+		updatedAt: updatedAt ?? createdAt ?? fallbackTimestamp,
+		agentSessionId: linkedAgentSessionIds[ linkedAgentSessionIds.length - 1 ],
+		linkedAgentSessionIds,
+	};
+}
+
+export async function listAiSessions(): Promise< AiSessionSummary[] > {
+	const sessionFiles = await listSessionFilesRecursively( getAiSessionsRootDirectory() );
+	const results = await Promise.allSettled(
+		sessionFiles.map( ( filePath ) => readAiSessionSummaryFromFile( filePath ) )
+	);
+
+	const sessions = results
+		.filter(
+			( result ): result is PromiseFulfilledResult< AiSessionSummary | undefined > =>
+				result.status === 'fulfilled'
+		)
+		.map( ( result ) => result.value )
+		.filter( ( session ): session is AiSessionSummary => !! session );
+
+	return sessions.sort( ( a, b ) => Date.parse( b.updatedAt ) - Date.parse( a.updatedAt ) );
+}
+
+export async function loadAiSession( sessionIdOrPrefix: string ): Promise< LoadedAiSession > {
+	const sessions = await listAiSessions();
+	const exactMatch = sessions.find( ( session ) => session.id === sessionIdOrPrefix );
+	const candidates = exactMatch
+		? [ exactMatch ]
+		: sessions.filter( ( session ) => session.id.startsWith( sessionIdOrPrefix ) );
+
+	if ( candidates.length === 0 ) {
+		throw new Error( `AI session not found: ${ sessionIdOrPrefix }` );
+	}
+
+	if ( candidates.length > 1 ) {
+		const sample = candidates
+			.slice( 0, 5 )
+			.map( ( session ) => session.id )
+			.join( ', ' );
+		throw new Error(
+			`Session id prefix is ambiguous: ${ sessionIdOrPrefix }. Matches: ${ sample }${
+				candidates.length > 5 ? ', …' : ''
+			}`
+		);
+	}
+
+	const summary = candidates[ 0 ];
+	const events = await readAiSessionEventsFromFile( summary.filePath );
+	return { summary, events };
+}
diff --git a/apps/cli/lib/tests/ai-sessions.test.ts b/apps/cli/lib/tests/ai-sessions.test.ts
index 26f963954c..ffae3eca54 100644
--- a/apps/cli/lib/tests/ai-sessions.test.ts
+++ b/apps/cli/lib/tests/ai-sessions.test.ts
@@ -5,6 +5,8 @@ import { afterEach, describe, expect, it } from 'vitest';
 import {
 	AiSessionRecorder,
 	getAiSessionsDirectoryForDate,
+	loadAiSession,
+	listAiSessions,
 	readAiSessionEventsFromFile,
 } from 'cli/lib/ai-sessions';
 
@@ -119,4 +121,60 @@ describe( 'ai-sessions', () => {
 			},
 		] );
 	} );
+
+	it( 'loads sessions by id prefix with linked Claude session metadata', async () => {
+		testRoot = await fs.mkdtemp( path.join( os.tmpdir(), 'studio-ai-sessions-' ) );
+		process.env.E2E = '1';
+		process.env.E2E_APP_DATA_PATH = testRoot;
+
+		const recorder = await AiSessionRecorder.create();
+		await recorder.recordUserMessage( {
+			text: 'Hello there',
+			source: 'prompt',
+		} );
+		await recorder.recordAgentSessionId( 'agent-session-123' );
+		await recorder.recordTurnClosed( 'success' );
+
+		const prefix = recorder.sessionId.slice( 0, 8 );
+		const loadedSession = await loadAiSession( prefix );
+		expect( loadedSession.summary.id ).toBe( recorder.sessionId );
+		expect( loadedSession.summary.agentSessionId ).toBe( 'agent-session-123' );
+		expect( loadedSession.summary.linkedAgentSessionIds ).toEqual( [ 'agent-session-123' ] );
+		expect( loadedSession.events.some( ( event ) => event.type === 'turn.closed' ) ).toBe( true );
+	} );
+
+	it( 'opens an existing session recorder and appends to the same file', async () => {
+		testRoot = await fs.mkdtemp( path.join( os.tmpdir(), 'studio-ai-sessions-' ) );
+		process.env.E2E = '1';
+		process.env.E2E_APP_DATA_PATH = testRoot;
+
+		const recorder = await AiSessionRecorder.create();
+		await recorder.recordAgentSessionId( 'agent-session-1' );
+		await recorder.recordUserMessage( {
+			text: 'First message',
+			source: 'prompt',
+		} );
+
+		const reopenedRecorder = await AiSessionRecorder.open( {
+			sessionId: recorder.sessionId,
+			filePath: recorder.filePath,
+			linkedAgentSessionIds: [ 'agent-session-1' ],
+		} );
+		await reopenedRecorder.recordTurnClosed( 'success' );
+
+		const sessions = await listAiSessions();
+		expect( sessions ).toHaveLength( 1 );
+		expect( sessions[ 0 ] ).toMatchObject( {
+			id: recorder.sessionId,
+			filePath: recorder.filePath,
+			agentSessionId: 'agent-session-1',
+			linkedAgentSessionIds: [ 'agent-session-1' ],
+		} );
+
+		const events = await readAiSessionEventsFromFile( recorder.filePath );
+		expect( events[ events.length - 1 ] ).toMatchObject( {
+			type: 'turn.closed',
+			status: 'success',
+		} );
+	} );
 } );

From 91feb84b4df622430aa409e60f7becc91c52263c Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Wed, 11 Mar 2026 15:18:53 +0100
Subject: [PATCH 04/33] Implement sessions listing command

---
 apps/cli/commands/ai.ts                | 171 ++++++++++++++++++++++++-
 apps/cli/lib/ai-sessions.ts            |  29 +++++
 apps/cli/lib/tests/ai-sessions.test.ts |  27 ++++
 3 files changed, 225 insertions(+), 2 deletions(-)

diff --git a/apps/cli/commands/ai.ts b/apps/cli/commands/ai.ts
index 084fabface..50643698fe 100644
--- a/apps/cli/commands/ai.ts
+++ b/apps/cli/commands/ai.ts
@@ -44,6 +44,155 @@ function getErrorMessage( error: unknown ): string {
 	return String( error );
 }
 
+function formatSessionTimestamp( timestamp: string ): string {
+	const parsed = Date.parse( timestamp );
+	if ( Number.isNaN( parsed ) ) {
+		return timestamp;
+	}
+
+	return new Date( parsed ).toISOString().replace( '.000Z', 'Z' ).replace( 'T', ' ' );
+}
+
+function getRelativeTime( timestamp: string ): string {
+	const targetMs = Date.parse( timestamp );
+	if ( Number.isNaN( targetMs ) ) {
+		return formatSessionTimestamp( timestamp );
+	}
+
+	const diffMs = targetMs - Date.now();
+	const absDiffMs = Math.abs( diffMs );
+	const rtf = new Intl.RelativeTimeFormat( undefined, { numeric: 'auto' } );
+	const units = [
+		{ unit: 'year', ms: 365 * 24 * 60 * 60 * 1000 },
+		{ unit: 'month', ms: 30 * 24 * 60 * 60 * 1000 },
+		{ unit: 'week', ms: 7 * 24 * 60 * 60 * 1000 },
+		{ unit: 'day', ms: 24 * 60 * 60 * 1000 },
+		{ unit: 'hour', ms: 60 * 60 * 1000 },
+		{ unit: 'minute', ms: 60 * 1000 },
+		{ unit: 'second', ms: 1000 },
+	] as const;
+
+	for ( const { unit, ms } of units ) {
+		if ( absDiffMs >= ms || unit === 'second' ) {
+			const value = Math.round( diffMs / ms );
+			return rtf.format( value, unit );
+		}
+	}
+
+	return formatSessionTimestamp( timestamp );
+}
+
+function toSingleLine( text: string ): string {
+	return text.replace( /\s+/g, ' ' ).trim();
+}
+
+function truncateWithEllipsis( text: string, maxLength: number ): string {
+	if ( text.length <= maxLength ) {
+		return text;
+	}
+
+	if ( maxLength <= 1 ) {
+		return '…';
+	}
+
+	return text.slice( 0, maxLength - 1 ) + '…';
+}
+
+function visibleWidth( text: string ): number {
+	return Array.from( text ).length;
+}
+
+function padEndVisible( text: string, width: number ): string {
+	return `${ text }${ ' '.repeat( Math.max( 0, width - visibleWidth( text ) ) ) }`;
+}
+
+function styleSessionId( id: string ): string {
+	return chalk.bold( id.slice( 0, 8 ) ) + chalk.dim( id.slice( 8 ) );
+}
+
+function formatSessionCompactLine(
+	session: AiSessionSummary,
+	terminalWidth: number,
+	layout: { idWidth: number; relativeWidth: number }
+): string {
+	const relative = getRelativeTime( session.updatedAt );
+	const prompt = toSingleLine( session.firstPrompt ?? __( '(No prompt yet)' ) );
+	const separator = chalk.dim( ' • ' );
+	const idText = padEndVisible( session.id, layout.idWidth );
+	const relativeText = padEndVisible( relative, layout.relativeWidth );
+	const hasStatusGlyph = session.endReason === 'error' || session.endReason === 'stopped';
+	const statusPlainWidth = hasStatusGlyph ? 2 : 0;
+	const siteLabelPlain = session.selectedSiteName ? `✻ ${ session.selectedSiteName }` : '';
+	const maxSiteLabelLength = Math.max( 8, Math.floor( terminalWidth * 0.25 ) );
+	const siteLabel = truncateWithEllipsis( siteLabelPlain, maxSiteLabelLength );
+	const suffixWidth = siteLabel ? visibleWidth( siteLabel ) : 0;
+	const gapWidth = siteLabel ? 2 : 0;
+	const prefixPlain = `${ idText } • ${ relativeText } • `;
+	const maxPromptLength = Math.max(
+		1,
+		terminalWidth - visibleWidth( prefixPlain ) - statusPlainWidth - gapWidth - suffixWidth - 1
+	);
+	const abstract = truncateWithEllipsis( prompt, maxPromptLength );
+	const promptStyled = session.firstPrompt ? chalk.white( abstract ) : chalk.dim( abstract );
+
+	const statusGlyph =
+		session.endReason === 'error'
+			? chalk.red( '✕ ' )
+			: session.endReason === 'stopped'
+			? chalk.gray( '◌ ' )
+			: '';
+	const leftPlain = `${ idText } • ${ relativeText } • ${ statusGlyph ? 'x ' : '' }${ abstract }`;
+	const renderedLeft = `${ styleSessionId( session.id ) }${ ' '.repeat(
+		Math.max( 0, layout.idWidth - visibleWidth( session.id ) )
+	) }${ separator }${ chalk.cyan( relative ) }${ ' '.repeat(
+		Math.max( 0, layout.relativeWidth - visibleWidth( relative ) )
+	) }${ separator }${ statusGlyph }${ promptStyled }`;
+	if ( ! siteLabel ) {
+		return renderedLeft;
+	}
+
+	const padding = Math.max(
+		2,
+		terminalWidth - visibleWidth( leftPlain ) - visibleWidth( siteLabel ) - 1
+	);
+	return `${ renderedLeft }${ ' '.repeat( padding ) }${ chalk.hex( '#8839ef' )( siteLabel ) }`;
+}
+
+function displaySessionsCompact( sessions: AiSessionSummary[] ): void {
+	const terminalWidth = Math.max( process.stdout.columns ?? 100, 60 );
+	const relativeTimes = sessions.map( ( session ) => getRelativeTime( session.updatedAt ) );
+	const layout = {
+		idWidth: Math.max( ...sessions.map( ( session ) => visibleWidth( session.id ) ) ),
+		relativeWidth: Math.max( ...relativeTimes.map( ( value ) => visibleWidth( value ) ) ),
+	};
+
+	console.log(
+		chalk.bold( __( 'AI Sessions' ) ) +
+			chalk.dim( ` (${ sessions.length })` ) +
+			chalk.dim( ` · ${ __( 'Most recent first' ) }` )
+	);
+
+	for ( const session of sessions ) {
+		console.log( formatSessionCompactLine( session, terminalWidth, layout ) );
+	}
+}
+
+async function runListSessionsCommand( format: 'compact' | 'json' ): Promise< void > {
+	const sessions = await listAiSessions();
+
+	if ( sessions.length === 0 ) {
+		console.log( __( 'No AI sessions found' ) );
+		return;
+	}
+
+	if ( format === 'json' ) {
+		console.log( JSON.stringify( sessions, null, 2 ) );
+		return;
+	}
+
+	displaySessionsCompact( sessions );
+}
+
 function extractAssistantMessageBlocks( message: SDKMessage ): AssistantMessageBlock[] {
 	if ( message.type !== 'assistant' ) {
 		return [];
@@ -508,8 +657,26 @@ export const registerCommand = ( yargs: StudioArgv ) => {
 							.command( {
 								command: 'list',
 								describe: __( 'List AI sessions' ),
-								handler: async () => {
-									// Not implemented
+								builder: ( listYargs ) => {
+									return listYargs.option( 'format', {
+										type: 'string',
+										choices: [ 'compact', 'json' ] as const,
+										default: 'compact' as const,
+										description: __( 'Output format' ),
+									} );
+								},
+								handler: async ( argv ) => {
+									try {
+										await runListSessionsCommand( argv.format as 'compact' | 'json' );
+									} catch ( error ) {
+										if ( error instanceof LoggerError ) {
+											logger.reportError( error );
+										} else {
+											logger.reportError(
+												new LoggerError( __( 'Failed to list AI sessions' ), error )
+											);
+										}
+									}
 								},
 							} )
 							.command( {
diff --git a/apps/cli/lib/ai-sessions.ts b/apps/cli/lib/ai-sessions.ts
index 61ab86f8a7..f3eb858f54 100644
--- a/apps/cli/lib/ai-sessions.ts
+++ b/apps/cli/lib/ai-sessions.ts
@@ -74,6 +74,10 @@ export interface AiSessionSummary {
 	updatedAt: string;
 	agentSessionId?: string;
 	linkedAgentSessionIds: string[];
+	firstPrompt?: string;
+	selectedSiteName?: string;
+	endReason?: 'error' | 'stopped';
+	eventCount: number;
 }
 
 export interface LoadedAiSession {
@@ -297,8 +301,13 @@ async function readAiSessionSummaryFromFile(
 	let createdAt: string | undefined;
 	let updatedAt: string | undefined;
 	let sessionId = getSessionIdFromPath( filePath );
+	let firstPrompt: string | undefined;
+	let selectedSiteName: string | undefined;
+	let endReason: 'error' | 'stopped' | undefined;
+	let eventCount = 0;
 
 	for ( const event of events ) {
+		eventCount += 1;
 		updatedAt = event.timestamp;
 
 		if ( event.type === 'session.started' ) {
@@ -314,6 +323,22 @@ async function readAiSessionSummaryFromFile(
 		) {
 			linkedAgentSessionIds.push( event.agentSessionId );
 		}
+
+		if ( event.type === 'site.selected' ) {
+			selectedSiteName = event.siteName;
+		}
+
+		if ( event.type === 'user.message' && event.source === 'prompt' && ! firstPrompt ) {
+			firstPrompt = event.text;
+		}
+
+		if ( event.type === 'turn.closed' ) {
+			if ( event.status === 'error' ) {
+				endReason = 'error';
+			} else if ( event.status === 'interrupted' ) {
+				endReason = 'stopped';
+			}
+		}
 	}
 
 	const stats = await fs.stat( filePath );
@@ -326,6 +351,10 @@ async function readAiSessionSummaryFromFile(
 		updatedAt: updatedAt ?? createdAt ?? fallbackTimestamp,
 		agentSessionId: linkedAgentSessionIds[ linkedAgentSessionIds.length - 1 ],
 		linkedAgentSessionIds,
+		firstPrompt,
+		selectedSiteName,
+		endReason,
+		eventCount,
 	};
 }
 
diff --git a/apps/cli/lib/tests/ai-sessions.test.ts b/apps/cli/lib/tests/ai-sessions.test.ts
index ffae3eca54..b2798e4d41 100644
--- a/apps/cli/lib/tests/ai-sessions.test.ts
+++ b/apps/cli/lib/tests/ai-sessions.test.ts
@@ -177,4 +177,31 @@ describe( 'ai-sessions', () => {
 			status: 'success',
 		} );
 	} );
+
+	it( 'builds list summaries with prompt, selected site, end reason, and event count', async () => {
+		testRoot = await fs.mkdtemp( path.join( os.tmpdir(), 'studio-ai-sessions-' ) );
+		process.env.E2E = '1';
+		process.env.E2E_APP_DATA_PATH = testRoot;
+
+		const recorder = await AiSessionRecorder.create();
+		await recorder.recordSiteSelected( {
+			name: 'My WordPress Website',
+			path: '/tmp/my-wordpress-website',
+		} );
+		await recorder.recordUserMessage( {
+			text: 'Create a homepage for me',
+			source: 'prompt',
+		} );
+		await recorder.recordTurnClosed( 'interrupted' );
+
+		const sessions = await listAiSessions();
+		expect( sessions ).toHaveLength( 1 );
+		expect( sessions[ 0 ] ).toMatchObject( {
+			id: recorder.sessionId,
+			firstPrompt: 'Create a homepage for me',
+			selectedSiteName: 'My WordPress Website',
+			endReason: 'stopped',
+		} );
+		expect( sessions[ 0 ].eventCount ).toBeGreaterThanOrEqual( 4 );
+	} );
 } );

From 7a0fedf768643e2e942675d46f591ad21a763e1d Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Wed, 11 Mar 2026 15:56:29 +0100
Subject: [PATCH 05/33] Save tool progress to sessions

---
 apps/cli/ai/ui.ts                      | 20 +++++++++++---------
 apps/cli/commands/ai.ts                | 18 +++++++-----------
 apps/cli/lib/ai-sessions.ts            | 17 +++++++++++++++++
 apps/cli/lib/tests/ai-sessions.test.ts |  5 +++++
 4 files changed, 40 insertions(+), 20 deletions(-)

diff --git a/apps/cli/ai/ui.ts b/apps/cli/ai/ui.ts
index 5813fe87d4..6c1830a3dd 100644
--- a/apps/cli/ai/ui.ts
+++ b/apps/cli/ai/ui.ts
@@ -247,9 +247,11 @@ const toolDisplayNames: Record< string, string > = {
 };
 
 export function getToolDetail( name: string, input: Record< string, unknown > ): string {
+	const fallbackDetail = typeof input.detail === 'string' ? input.detail : '';
+
 	switch ( name ) {
 		case 'mcp__studio__site_create':
-			return typeof input.name === 'string' ? input.name : '';
+			return typeof input.name === 'string' ? input.name : fallbackDetail;
 		case 'mcp__studio__site_info':
 		case 'mcp__studio__site_start':
 		case 'mcp__studio__site_stop':
@@ -261,14 +263,14 @@ export function getToolDetail( name: string, input: Record< string, unknown > ):
 		case 'mcp__studio__preview_delete':
 			return typeof input.host === 'string' ? input.host : '';
 		case 'mcp__studio__wp_cli':
-			return typeof input.command === 'string' ? `wp ${ input.command }` : '';
+			return typeof input.command === 'string' ? `wp ${ input.command }` : fallbackDetail;
 		case 'mcp__studio__validate_blocks':
 			if ( typeof input.filePath === 'string' ) {
 				return input.filePath.split( '/' ).slice( -2 ).join( '/' );
 			}
-			return 'inline content';
+			return fallbackDetail || 'inline content';
 		case 'mcp__studio__take_screenshot':
-			return typeof input.url === 'string' ? input.url : '';
+			return typeof input.url === 'string' ? input.url : fallbackDetail;
 		case 'Read':
 		case 'Write':
 		case 'Edit': {
@@ -277,21 +279,21 @@ export function getToolDetail( name: string, input: Record< string, unknown > ):
 				const parts = filePath.split( '/' );
 				return parts.slice( -2 ).join( '/' );
 			}
-			return '';
+			return fallbackDetail;
 		}
 		case 'Bash':
 			return typeof input.command === 'string'
 				? input.command.length > 60
 					? input.command.slice( 0, 57 ) + '…'
 					: input.command
-				: '';
+				: fallbackDetail;
 		case 'Skill':
-			return typeof input.skill === 'string' ? input.skill : '';
+			return typeof input.skill === 'string' ? input.skill : fallbackDetail;
 		case 'Grep':
 		case 'Glob':
-			return typeof input.pattern === 'string' ? input.pattern : '';
+			return typeof input.pattern === 'string' ? input.pattern : fallbackDetail;
 		default:
-			return typeof input.detail === 'string' ? input.detail : '';
+			return fallbackDetail;
 	}
 }
 
diff --git a/apps/cli/commands/ai.ts b/apps/cli/commands/ai.ts
index 50643698fe..705e71a28b 100644
--- a/apps/cli/commands/ai.ts
+++ b/apps/cli/commands/ai.ts
@@ -281,7 +281,7 @@ function extractToolResult( message: SDKMessage ): { ok: boolean; text: string }
 		const text = String( rawResult ).trim();
 		return {
 			ok: true,
-			text: text || 'Tool completed with no textual output.',
+			text,
 		};
 	}
 
@@ -293,18 +293,9 @@ function extractToolResult( message: SDKMessage ): { ok: boolean; text: string }
 	const isError = typedResult.isError === true || typedResult.is_error === true;
 	const textFromContent = toToolResultText( typedResult.content );
 
-	if ( textFromContent ) {
-		return {
-			ok: ! isError,
-			text: textFromContent,
-		};
-	}
-
 	return {
 		ok: ! isError,
-		text: isError
-			? 'Tool returned an error with no textual output.'
-			: 'Tool completed with no textual output.',
+		text: textFromContent,
 	};
 }
 
@@ -351,6 +342,11 @@ export async function runCommand(): Promise< void > {
 		}
 	};
 
+	setProgressCallback( ( message ) => {
+		ui.setLoaderMessage( message );
+		void persist( ( recorder ) => recorder.recordToolProgress( message ) );
+	} );
+
 	let currentModel: AiModelId = DEFAULT_MODEL;
 
 	async function prepareProviderSelection(
diff --git a/apps/cli/lib/ai-sessions.ts b/apps/cli/lib/ai-sessions.ts
index f3eb858f54..0d20bc3365 100644
--- a/apps/cli/lib/ai-sessions.ts
+++ b/apps/cli/lib/ai-sessions.ts
@@ -52,6 +52,11 @@ export type AiSessionEvent =
 			ok: boolean;
 			text: string;
 	  }
+	| {
+			type: 'tool.progress';
+			timestamp: string;
+			message: string;
+	  }
 	| {
 			type: 'agent.question';
 			timestamp: string;
@@ -205,6 +210,18 @@ export class AiSessionRecorder {
 		} );
 	}
 
+	async recordToolProgress( message: string ): Promise< void > {
+		if ( ! message.trim() ) {
+			return;
+		}
+
+		await this.appendEvent( {
+			type: 'tool.progress',
+			timestamp: toIsoTimestamp(),
+			message,
+		} );
+	}
+
 	async recordAgentQuestion( options: {
 		question: string;
 		options: Array< {
diff --git a/apps/cli/lib/tests/ai-sessions.test.ts b/apps/cli/lib/tests/ai-sessions.test.ts
index b2798e4d41..c0e67ee510 100644
--- a/apps/cli/lib/tests/ai-sessions.test.ts
+++ b/apps/cli/lib/tests/ai-sessions.test.ts
@@ -48,6 +48,7 @@ describe( 'ai-sessions', () => {
 			ok: true,
 			text: 'File read successfully',
 		} );
+		await recorder.recordToolProgress( 'Starting process daemon…' );
 		await recorder.recordAgentQuestion( {
 			question: 'Choose a plugin slug',
 			options: [
@@ -86,6 +87,10 @@ describe( 'ai-sessions', () => {
 				{ type: 'tool_use', name: 'Read' },
 			],
 		} );
+		expect( events.find( ( event ) => event.type === 'tool.progress' ) ).toMatchObject( {
+			type: 'tool.progress',
+			message: 'Starting process daemon…',
+		} );
 		expect( events.find( ( event ) => event.type === 'turn.closed' ) ).toMatchObject( {
 			type: 'turn.closed',
 			status: 'success',

From def97f90802f544c6afe29a928a51f5011ee1764 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Wed, 11 Mar 2026 15:59:27 +0100
Subject: [PATCH 06/33] Add support for "latest" argument in sessions resume

---
 apps/cli/commands/ai.ts | 8 +++++++-
 1 file changed, 7 insertions(+), 1 deletion(-)

diff --git a/apps/cli/commands/ai.ts b/apps/cli/commands/ai.ts
index 705e71a28b..88ba7e5599 100644
--- a/apps/cli/commands/ai.ts
+++ b/apps/cli/commands/ai.ts
@@ -677,7 +677,13 @@ export const registerCommand = ( yargs: StudioArgv ) => {
 							} )
 							.command( {
 								command: 'resume <id>',
-								describe: __( 'Resume an AI session' ),
+								describe: __( 'Resume an AI session (id or "latest")' ),
+								builder: ( resumeYargs ) => {
+									return resumeYargs.positional( 'id', {
+										type: 'string',
+										describe: __( 'Session id (or "latest")' ),
+									} );
+								},
 								handler: async ( argv ) => {
 									try {
 										await runResumeSessionCommand( argv.id as string );

From 3b5776e74208310db7d0916a548d3c415bd7259c Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Wed, 11 Mar 2026 16:06:26 +0100
Subject: [PATCH 07/33] Implement sessions delete command

---
 apps/cli/commands/ai.ts                | 22 +++++++++--
 apps/cli/lib/ai-sessions.ts            | 53 ++++++++++++++++++++++++++
 apps/cli/lib/tests/ai-sessions.test.ts | 30 +++++++++++++++
 3 files changed, 102 insertions(+), 3 deletions(-)

diff --git a/apps/cli/commands/ai.ts b/apps/cli/commands/ai.ts
index 88ba7e5599..cc5c24c147 100644
--- a/apps/cli/commands/ai.ts
+++ b/apps/cli/commands/ai.ts
@@ -702,9 +702,25 @@ export const registerCommand = ( yargs: StudioArgv ) => {
 							} )
 							.command( {
 								command: 'delete <id>',
-								describe: __( 'Delete an AI session' ),
-								handler: async () => {
-									// Not implemented
+								describe: __( 'Delete an AI session (id, prefix, or "latest")' ),
+								builder: ( deleteYargs ) => {
+									return deleteYargs.positional( 'id', {
+										type: 'string',
+										describe: __( 'Session id, id prefix, or "latest"' ),
+									} );
+								},
+								handler: async ( argv ) => {
+									try {
+										await runDeleteSessionCommand( argv.id as string );
+									} catch ( error ) {
+										if ( error instanceof LoggerError ) {
+											logger.reportError( error );
+										} else {
+											logger.reportError(
+												new LoggerError( __( 'Failed to delete AI session' ), error )
+											);
+										}
+									}
 								},
 							} )
 							.version( false )
diff --git a/apps/cli/lib/ai-sessions.ts b/apps/cli/lib/ai-sessions.ts
index 0d20bc3365..1467c15688 100644
--- a/apps/cli/lib/ai-sessions.ts
+++ b/apps/cli/lib/ai-sessions.ts
@@ -419,3 +419,56 @@ export async function loadAiSession( sessionIdOrPrefix: string ): Promise< Loade
 	const events = await readAiSessionEventsFromFile( summary.filePath );
 	return { summary, events };
 }
+
+async function pruneEmptySessionDirectories( startDirectory: string ): Promise< void > {
+	const rootDirectory = getAiSessionsRootDirectory();
+	let currentDirectory = startDirectory;
+
+	while (
+		currentDirectory.startsWith( rootDirectory + path.sep ) &&
+		currentDirectory !== rootDirectory
+	) {
+		try {
+			await fs.rmdir( currentDirectory );
+		} catch ( error ) {
+			const fsError = error as NodeJS.ErrnoException;
+			if ( fsError.code === 'ENOTEMPTY' || fsError.code === 'ENOENT' ) {
+				return;
+			}
+
+			throw error;
+		}
+
+		currentDirectory = path.dirname( currentDirectory );
+	}
+}
+
+export async function deleteAiSession( sessionIdOrPrefix: string ): Promise< AiSessionSummary > {
+	const sessions = await listAiSessions();
+	const exactMatch = sessions.find( ( session ) => session.id === sessionIdOrPrefix );
+	const candidates = exactMatch
+		? [ exactMatch ]
+		: sessions.filter( ( session ) => session.id.startsWith( sessionIdOrPrefix ) );
+
+	if ( candidates.length === 0 ) {
+		throw new Error( `AI session not found: ${ sessionIdOrPrefix }` );
+	}
+
+	if ( candidates.length > 1 ) {
+		const sample = candidates
+			.slice( 0, 5 )
+			.map( ( session ) => session.id )
+			.join( ', ' );
+		throw new Error(
+			`Session id prefix is ambiguous: ${ sessionIdOrPrefix }. Matches: ${ sample }${
+				candidates.length > 5 ? ', …' : ''
+			}`
+		);
+	}
+
+	const sessionToDelete = candidates[ 0 ];
+	await fs.rm( sessionToDelete.filePath, { force: false } );
+	await pruneEmptySessionDirectories( path.dirname( sessionToDelete.filePath ) );
+
+	return sessionToDelete;
+}
diff --git a/apps/cli/lib/tests/ai-sessions.test.ts b/apps/cli/lib/tests/ai-sessions.test.ts
index c0e67ee510..6a199d52fa 100644
--- a/apps/cli/lib/tests/ai-sessions.test.ts
+++ b/apps/cli/lib/tests/ai-sessions.test.ts
@@ -4,7 +4,9 @@ import path from 'path';
 import { afterEach, describe, expect, it } from 'vitest';
 import {
 	AiSessionRecorder,
+	deleteAiSession,
 	getAiSessionsDirectoryForDate,
+	getAiSessionsRootDirectory,
 	loadAiSession,
 	listAiSessions,
 	readAiSessionEventsFromFile,
@@ -209,4 +211,32 @@ describe( 'ai-sessions', () => {
 		} );
 		expect( sessions[ 0 ].eventCount ).toBeGreaterThanOrEqual( 4 );
 	} );
+
+	it( 'deletes a session by id prefix and prunes empty date directories', async () => {
+		testRoot = await fs.mkdtemp( path.join( os.tmpdir(), 'studio-ai-sessions-' ) );
+		process.env.E2E = '1';
+		process.env.E2E_APP_DATA_PATH = testRoot;
+
+		const startedAt = new Date( '2026-03-11T10:00:00.000Z' );
+		const recorder = await AiSessionRecorder.create( { startedAt } );
+		await recorder.recordUserMessage( {
+			text: 'Delete me',
+			source: 'prompt',
+		} );
+
+		const deleted = await deleteAiSession( recorder.sessionId.slice( 0, 8 ) );
+		expect( deleted.id ).toBe( recorder.sessionId );
+
+		const sessions = await listAiSessions();
+		expect( sessions ).toHaveLength( 0 );
+
+		const dayDirectory = getAiSessionsDirectoryForDate( startedAt );
+		const monthDirectory = path.dirname( dayDirectory );
+		const yearDirectory = path.dirname( monthDirectory );
+		await expect( fs.access( dayDirectory ) ).rejects.toThrow();
+		await expect( fs.access( monthDirectory ) ).rejects.toThrow();
+		await expect( fs.access( yearDirectory ) ).rejects.toThrow();
+
+		await expect( fs.access( getAiSessionsRootDirectory() ) ).resolves.not.toThrow();
+	} );
 } );

From d358405c4b881861d16bcca109fee055497fbe84 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Wed, 11 Mar 2026 16:18:04 +0100
Subject: [PATCH 08/33] Add timestamp to sessions filename

---
 apps/cli/lib/ai-sessions.ts            | 16 ++++++++++++++--
 apps/cli/lib/tests/ai-sessions.test.ts |  2 ++
 2 files changed, 16 insertions(+), 2 deletions(-)

diff --git a/apps/cli/lib/ai-sessions.ts b/apps/cli/lib/ai-sessions.ts
index 1467c15688..8dbde331d5 100644
--- a/apps/cli/lib/ai-sessions.ts
+++ b/apps/cli/lib/ai-sessions.ts
@@ -98,6 +98,13 @@ function formatDatePart( value: number ): string {
 	return String( value ).padStart( 2, '0' );
 }
 
+function toSortableTimestampPrefix( date: Date ): string {
+	return date
+		.toISOString()
+		.replace( /:/g, '-' )
+		.replace( /\.\d{3}Z$/, '' );
+}
+
 export function getAiSessionsDirectoryForDate( date: Date ): string {
 	const year = String( date.getFullYear() );
 	const month = formatDatePart( date.getMonth() + 1 );
@@ -125,7 +132,8 @@ export class AiSessionRecorder {
 		const startedAt = options.startedAt ?? new Date();
 		const sessionId = crypto.randomUUID();
 		const directory = getAiSessionsDirectoryForDate( startedAt );
-		const filePath = path.join( directory, `${ sessionId }.jsonl` );
+		const fileName = `${ toSortableTimestampPrefix( startedAt ) }-${ sessionId }.jsonl`;
+		const filePath = path.join( directory, fileName );
 
 		await fs.mkdir( directory, { recursive: true } );
 
@@ -272,7 +280,11 @@ export async function readAiSessionEventsFromFile( filePath: string ): Promise<
 }
 
 function getSessionIdFromPath( filePath: string ): string {
-	return path.basename( filePath, '.jsonl' );
+	const fileName = path.basename( filePath, '.jsonl' );
+	const uuidMatch = fileName.match(
+		/\b([0-9a-f]{8}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{12})\b/i
+	);
+	return uuidMatch?.[ 1 ] ?? fileName;
 }
 
 async function listSessionFilesRecursively( directory: string ): Promise< string[] > {
diff --git a/apps/cli/lib/tests/ai-sessions.test.ts b/apps/cli/lib/tests/ai-sessions.test.ts
index 6a199d52fa..f78c266f61 100644
--- a/apps/cli/lib/tests/ai-sessions.test.ts
+++ b/apps/cli/lib/tests/ai-sessions.test.ts
@@ -71,6 +71,8 @@ describe( 'ai-sessions', () => {
 		expect( recorder.filePath.startsWith( getAiSessionsDirectoryForDate( startedAt ) ) ).toBe(
 			true
 		);
+		const fileName = path.basename( recorder.filePath );
+		expect( fileName ).toBe( `2026-03-11T10-00-00-${ recorder.sessionId }.jsonl` );
 		expect( events[ 0 ] ).toMatchObject( {
 			type: 'session.started',
 			version: 1,

From 63026e7b553491f8319e950380f18ae33c417b8b Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Wed, 11 Mar 2026 16:23:32 +0100
Subject: [PATCH 09/33] Add sessions browser for agument-less delete and resume
 commands

---
 apps/cli/commands/ai.ts | 91 +++++++++++++++++++++++++++++++++++++----
 1 file changed, 84 insertions(+), 7 deletions(-)

diff --git a/apps/cli/commands/ai.ts b/apps/cli/commands/ai.ts
index cc5c24c147..324512b8d5 100644
--- a/apps/cli/commands/ai.ts
+++ b/apps/cli/commands/ai.ts
@@ -193,6 +193,79 @@ async function runListSessionsCommand( format: 'compact' | 'json' ): Promise< vo
 	displaySessionsCompact( sessions );
 }
 
+async function pickSessionInteractively(
+	sessions: AiSessionSummary[],
+	message: string
+): Promise< AiSessionSummary | undefined > {
+	const interactiveWidth = Math.max( ( process.stdout.columns ?? 100 ) - 4, 56 );
+	const abortController = new AbortController();
+	const handleEscKey = ( chunk: Buffer | string ) => {
+		const bytes = Buffer.isBuffer( chunk ) ? chunk : Buffer.from( chunk );
+		if ( bytes.length === 1 && bytes[ 0 ] === 0x1b ) {
+			abortController.abort();
+		}
+	};
+
+	if ( process.stdin.isTTY ) {
+		process.stdin.on( 'data', handleEscKey );
+	}
+
+	try {
+		const selectedSessionId = await select(
+			{
+				message,
+				choices: sessions.map( ( session ) => ( {
+					name: formatSessionCompactLine( session, interactiveWidth, {
+						idWidth: Math.max( ...sessions.map( ( s ) => visibleWidth( s.id ) ) ),
+						relativeWidth: Math.max(
+							...sessions.map( ( s ) => visibleWidth( getRelativeTime( s.updatedAt ) ) )
+						),
+					} ),
+					value: session.id,
+				} ) ),
+				pageSize: Math.min( 12, sessions.length ),
+				loop: false,
+				theme: {
+					style: {
+						keysHelpTip: () => chalk.dim( '↑↓ navigate · ⏎ select · esc cancel' ),
+					},
+				},
+			},
+			{
+				signal: abortController.signal,
+			}
+		);
+
+		return sessions.find( ( session ) => session.id === selectedSessionId );
+	} catch ( error ) {
+		if (
+			error instanceof Error &&
+			( error.name === 'AbortPromptError' || error.name === 'ExitPromptError' )
+		) {
+			return undefined;
+		}
+
+		throw error;
+	} finally {
+		if ( process.stdin.isTTY ) {
+			process.stdin.off( 'data', handleEscKey );
+		}
+	}
+}
+
+async function chooseSessionForAction(
+	actionLabel: string,
+	noSessionsMessage: string
+): Promise< AiSessionSummary | undefined > {
+	const sessions = await listAiSessions();
+	if ( sessions.length === 0 ) {
+		console.log( noSessionsMessage );
+		return undefined;
+	}
+
+	return pickSessionInteractively( sessions, actionLabel );
+}
+
 function extractAssistantMessageBlocks( message: SDKMessage ): AssistantMessageBlock[] {
 	if ( message.type !== 'assistant' ) {
 		return [];
@@ -676,17 +749,19 @@ export const registerCommand = ( yargs: StudioArgv ) => {
 								},
 							} )
 							.command( {
-								command: 'resume <id>',
-								describe: __( 'Resume an AI session (id or "latest")' ),
+								command: 'resume [id]',
+								describe: __( 'Resume an AI session (id, prefix, "latest", or picker)' ),
 								builder: ( resumeYargs ) => {
 									return resumeYargs.positional( 'id', {
 										type: 'string',
-										describe: __( 'Session id (or "latest")' ),
+										describe: __( 'Session id, id prefix, or "latest"' ),
 									} );
 								},
 								handler: async ( argv ) => {
 									try {
-										await runResumeSessionCommand( argv.id as string );
+										await runResumeSessionCommand(
+											typeof argv.id === 'string' ? argv.id : undefined
+										);
 									} catch ( error ) {
 										if ( error instanceof LoggerError ) {
 											logger.reportError( error );
@@ -701,8 +776,8 @@ export const registerCommand = ( yargs: StudioArgv ) => {
 								},
 							} )
 							.command( {
-								command: 'delete <id>',
-								describe: __( 'Delete an AI session (id, prefix, or "latest")' ),
+								command: 'delete [id]',
+								describe: __( 'Delete an AI session (id, prefix, "latest", or picker)' ),
 								builder: ( deleteYargs ) => {
 									return deleteYargs.positional( 'id', {
 										type: 'string',
@@ -711,7 +786,9 @@ export const registerCommand = ( yargs: StudioArgv ) => {
 								},
 								handler: async ( argv ) => {
 									try {
-										await runDeleteSessionCommand( argv.id as string );
+										await runDeleteSessionCommand(
+											typeof argv.id === 'string' ? argv.id : undefined
+										);
 									} catch ( error ) {
 										if ( error instanceof LoggerError ) {
 											logger.reportError( error );

From 2b2fc5f2f90b7b59b1d32a069383b8572d386416 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Wed, 11 Mar 2026 19:21:09 +0100
Subject: [PATCH 10/33] Add additional ai and ai-sessions tests cases

---
 apps/cli/commands/tests/ai.test.ts     | 236 +++++++++++++++++++++++++
 apps/cli/lib/tests/ai-sessions.test.ts |  74 ++++++++
 2 files changed, 310 insertions(+)
 create mode 100644 apps/cli/commands/tests/ai.test.ts

diff --git a/apps/cli/commands/tests/ai.test.ts b/apps/cli/commands/tests/ai.test.ts
new file mode 100644
index 0000000000..d707e5984a
--- /dev/null
+++ b/apps/cli/commands/tests/ai.test.ts
@@ -0,0 +1,236 @@
+import { beforeEach, describe, expect, it, vi } from 'vitest';
+import yargs from 'yargs/yargs';
+import { registerCommand } from 'cli/commands/ai';
+import {
+	AiSessionRecorder,
+	deleteAiSession,
+	listAiSessions,
+	loadAiSession,
+} from 'cli/lib/ai-sessions';
+import { getAnthropicApiKey } from 'cli/lib/appdata';
+import { StudioArgv } from 'cli/types';
+
+const { reportErrorMock } = vi.hoisted( () => ( {
+	reportErrorMock: vi.fn(),
+} ) );
+
+vi.mock( 'cli/lib/appdata', () => ( {
+	getAnthropicApiKey: vi.fn(),
+	saveAnthropicApiKey: vi.fn(),
+} ) );
+
+vi.mock( 'cli/logger', () => ( {
+	Logger: class {
+		reportStart = vi.fn();
+		reportSuccess = vi.fn();
+		reportError = reportErrorMock;
+		reportProgress = vi.fn();
+		reportWarning = vi.fn();
+		reportKeyValuePair = vi.fn();
+		spinner = {};
+		currentAction = null;
+	},
+	LoggerError: class LoggerError extends Error {
+		previousError?: Error;
+		constructor( message: string, previousError?: unknown ) {
+			super(
+				previousError instanceof Error ? `${ message }: ${ previousError.message }` : message
+			);
+			this.name = 'LoggerError';
+			if ( previousError instanceof Error ) {
+				this.previousError = previousError;
+			}
+		}
+	},
+	setProgressCallback: vi.fn(),
+} ) );
+
+vi.mock( 'cli/ai/agent', () => {
+	const emptyQuery = {
+		interrupt: vi.fn().mockResolvedValue( undefined ),
+		[ Symbol.asyncIterator ]() {
+			return {
+				next: async () => ( {
+					done: true as const,
+					value: undefined,
+				} ),
+			};
+		},
+	};
+
+	return {
+		AI_MODELS: {
+			'claude-sonnet-4-6': 'Sonnet 4.6',
+			'claude-opus-4-6': 'Opus 4.6',
+		},
+		DEFAULT_MODEL: 'claude-sonnet-4-6',
+		startAiAgent: vi.fn( () => emptyQuery ),
+	};
+} );
+
+vi.mock( 'cli/ai/ui', () => ( {
+	AiChatUI: class {
+		activeSite: { name: string; path: string; running: boolean } | null = null;
+		currentModel = 'claude-sonnet-4-6';
+		onSiteSelected: ( ( site: { name: string; path: string; running: boolean } ) => void ) | null =
+			null;
+		onInterrupt: ( () => void ) | null = null;
+		start() {}
+		stop() {}
+		showWelcome() {}
+		showInfo() {}
+		showError() {}
+		prepareForReplay() {}
+		finishReplay() {}
+		beginAgentTurn() {}
+		endAgentTurn() {}
+		setLoaderMessage() {}
+		setActiveSite( site: { name: string; path: string; running: boolean } ) {
+			this.activeSite = site;
+		}
+		addUserMessage() {}
+		handleMessage() {
+			return undefined;
+		}
+		showAgentQuestion() {}
+		async askUser() {
+			return {};
+		}
+		async waitForInput() {
+			return '/exit';
+		}
+	},
+	getToolDetail: ( _name: string, input: Record< string, unknown > ) =>
+		typeof input.detail === 'string' ? input.detail : '',
+} ) );
+
+vi.mock( 'cli/lib/ai-sessions', () => {
+	class MockAiSessionRecorder {
+		static create = vi.fn().mockResolvedValue( new MockAiSessionRecorder() );
+		static open = vi.fn().mockResolvedValue( new MockAiSessionRecorder() );
+		async recordToolProgress() {}
+		async recordSiteSelected() {}
+		async recordUserMessage() {}
+		async recordAssistantMessage() {}
+		async recordToolResult() {}
+		async recordAgentQuestion() {}
+		async recordTurnClosed() {}
+		async recordAgentSessionId() {}
+	}
+
+	return {
+		AiSessionRecorder: MockAiSessionRecorder,
+		listAiSessions: vi.fn(),
+		loadAiSession: vi.fn(),
+		deleteAiSession: vi.fn(),
+	};
+} );
+
+describe( 'CLI: studio ai sessions command', () => {
+	beforeEach( () => {
+		vi.clearAllMocks();
+		vi.mocked( getAnthropicApiKey ).mockResolvedValue( 'test-api-key' );
+		vi.spyOn( process, 'exit' ).mockImplementation( () => undefined as never );
+	} );
+
+	function buildParser(): StudioArgv {
+		const parser = yargs( [] ).scriptName( 'studio' ).strict().exitProcess( false ) as StudioArgv;
+		registerCommand( parser );
+		return parser;
+	}
+
+	it( 'resumes the latest session', async () => {
+		vi.mocked( listAiSessions ).mockResolvedValue( [
+			{
+				id: 'session-latest',
+				filePath: '/tmp/session-latest.jsonl',
+				createdAt: '2026-03-11T11:00:00.000Z',
+				updatedAt: '2026-03-11T11:00:00.000Z',
+				linkedAgentSessionIds: [],
+				eventCount: 1,
+			},
+			{
+				id: 'session-older',
+				filePath: '/tmp/session-older.jsonl',
+				createdAt: '2026-03-10T11:00:00.000Z',
+				updatedAt: '2026-03-10T11:00:00.000Z',
+				linkedAgentSessionIds: [],
+				eventCount: 1,
+			},
+		] );
+		vi.mocked( loadAiSession ).mockResolvedValue( {
+			summary: {
+				id: 'session-latest',
+				filePath: '/tmp/session-latest.jsonl',
+				createdAt: '2026-03-11T11:00:00.000Z',
+				updatedAt: '2026-03-11T11:00:00.000Z',
+				linkedAgentSessionIds: [],
+				eventCount: 1,
+			},
+			events: [],
+		} );
+
+		await buildParser().parseAsync( [ 'ai', 'sessions', 'resume', 'latest' ] );
+
+		expect( loadAiSession ).toHaveBeenCalledWith( 'session-latest' );
+		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).open ).toHaveBeenCalledWith(
+			expect.objectContaining( {
+				sessionId: 'session-latest',
+				filePath: '/tmp/session-latest.jsonl',
+			} )
+		);
+		expect( process.exit ).toHaveBeenCalledWith( 0 );
+	} );
+
+	it( 'deletes the latest session', async () => {
+		vi.mocked( listAiSessions ).mockResolvedValue( [
+			{
+				id: 'session-latest',
+				filePath: '/tmp/session-latest.jsonl',
+				createdAt: '2026-03-11T11:00:00.000Z',
+				updatedAt: '2026-03-11T11:00:00.000Z',
+				linkedAgentSessionIds: [],
+				eventCount: 1,
+			},
+			{
+				id: 'session-older',
+				filePath: '/tmp/session-older.jsonl',
+				createdAt: '2026-03-10T11:00:00.000Z',
+				updatedAt: '2026-03-10T11:00:00.000Z',
+				linkedAgentSessionIds: [],
+				eventCount: 1,
+			},
+		] );
+		vi.mocked( deleteAiSession ).mockResolvedValue( {
+			id: 'session-latest',
+			filePath: '/tmp/session-latest.jsonl',
+			createdAt: '2026-03-11T11:00:00.000Z',
+			updatedAt: '2026-03-11T11:00:00.000Z',
+			linkedAgentSessionIds: [],
+			eventCount: 1,
+		} );
+
+		await buildParser().parseAsync( [ 'ai', 'sessions', 'delete', 'latest' ] );
+
+		expect( deleteAiSession ).toHaveBeenCalledWith( 'session-latest' );
+		expect( console.log ).toHaveBeenCalledWith( expect.stringContaining( 'session-latest' ) );
+	} );
+
+	it( 'reports an error when resuming latest and no sessions exist', async () => {
+		vi.mocked( listAiSessions ).mockResolvedValue( [] );
+
+		await buildParser().parseAsync( [ 'ai', 'sessions', 'resume', 'latest' ] );
+
+		expect( loadAiSession ).not.toHaveBeenCalled();
+		expect( reportErrorMock ).toHaveBeenCalled();
+	} );
+
+	it( 'reports an error when deleting latest and no sessions exist', async () => {
+		vi.mocked( listAiSessions ).mockResolvedValue( [] );
+
+		await buildParser().parseAsync( [ 'ai', 'sessions', 'delete', 'latest' ] );
+
+		expect( deleteAiSession ).not.toHaveBeenCalled();
+		expect( reportErrorMock ).toHaveBeenCalled();
+	} );
+} );
diff --git a/apps/cli/lib/tests/ai-sessions.test.ts b/apps/cli/lib/tests/ai-sessions.test.ts
index f78c266f61..78f0955809 100644
--- a/apps/cli/lib/tests/ai-sessions.test.ts
+++ b/apps/cli/lib/tests/ai-sessions.test.ts
@@ -241,4 +241,78 @@ describe( 'ai-sessions', () => {
 
 		await expect( fs.access( getAiSessionsRootDirectory() ) ).resolves.not.toThrow();
 	} );
+
+	it( 'keeps date directories when deleting one of multiple sessions from the same day', async () => {
+		testRoot = await fs.mkdtemp( path.join( os.tmpdir(), 'studio-ai-sessions-' ) );
+		process.env.E2E = '1';
+		process.env.E2E_APP_DATA_PATH = testRoot;
+
+		const firstStart = new Date( '2026-03-11T10:00:00.000Z' );
+		const secondStart = new Date( '2026-03-11T11:00:00.000Z' );
+		const firstRecorder = await AiSessionRecorder.create( { startedAt: firstStart } );
+		const secondRecorder = await AiSessionRecorder.create( { startedAt: secondStart } );
+
+		await firstRecorder.recordUserMessage( {
+			text: 'Delete me',
+			source: 'prompt',
+		} );
+		await secondRecorder.recordUserMessage( {
+			text: 'Keep me',
+			source: 'prompt',
+		} );
+
+		await deleteAiSession( firstRecorder.sessionId );
+
+		const sessions = await listAiSessions();
+		expect( sessions ).toHaveLength( 1 );
+		expect( sessions[ 0 ].id ).toBe( secondRecorder.sessionId );
+
+		const dayDirectory = getAiSessionsDirectoryForDate( firstStart );
+		const monthDirectory = path.dirname( dayDirectory );
+		const yearDirectory = path.dirname( monthDirectory );
+
+		await expect( fs.access( dayDirectory ) ).resolves.not.toThrow();
+		await expect( fs.access( monthDirectory ) ).resolves.not.toThrow();
+		await expect( fs.access( yearDirectory ) ).resolves.not.toThrow();
+	} );
+
+	it( 'throws when deleting a missing session id or prefix', async () => {
+		testRoot = await fs.mkdtemp( path.join( os.tmpdir(), 'studio-ai-sessions-' ) );
+		process.env.E2E = '1';
+		process.env.E2E_APP_DATA_PATH = testRoot;
+
+		await expect( deleteAiSession( 'does-not-exist' ) ).rejects.toThrow(
+			'AI session not found: does-not-exist'
+		);
+	} );
+
+	it( 'throws when deleting an ambiguous id prefix', async () => {
+		testRoot = await fs.mkdtemp( path.join( os.tmpdir(), 'studio-ai-sessions-' ) );
+		process.env.E2E = '1';
+		process.env.E2E_APP_DATA_PATH = testRoot;
+
+		await AiSessionRecorder.create( { startedAt: new Date( '2026-03-11T10:00:00.000Z' ) } );
+		await AiSessionRecorder.create( { startedAt: new Date( '2026-03-11T11:00:00.000Z' ) } );
+
+		await expect( deleteAiSession( '' ) ).rejects.toThrow( 'Session id prefix is ambiguous' );
+	} );
+
+	it( 'lists sessions with most recent update first (latest semantics)', async () => {
+		testRoot = await fs.mkdtemp( path.join( os.tmpdir(), 'studio-ai-sessions-' ) );
+		process.env.E2E = '1';
+		process.env.E2E_APP_DATA_PATH = testRoot;
+
+		const older = await AiSessionRecorder.create( {
+			startedAt: new Date( '2026-03-10T10:00:00.000Z' ),
+		} );
+		const latest = await AiSessionRecorder.create( {
+			startedAt: new Date( '2026-03-11T10:00:00.000Z' ),
+		} );
+
+		const sessions = await listAiSessions();
+		expect( sessions.map( ( session ) => session.id ) ).toEqual( [
+			latest.sessionId,
+			older.sessionId,
+		] );
+	} );
 } );

From 60b9c6242be68afb26abe7a464a233636b281577 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Wed, 11 Mar 2026 20:02:30 +0100
Subject: [PATCH 11/33] Add a --no-session-persistence flag

---
 apps/cli/commands/ai.ts            | 50 ++++++++++++++++++++----------
 apps/cli/commands/tests/ai.test.ts | 49 +++++++++++++++++++++++++++++
 2 files changed, 83 insertions(+), 16 deletions(-)

diff --git a/apps/cli/commands/ai.ts b/apps/cli/commands/ai.ts
index 324512b8d5..703adff3c1 100644
--- a/apps/cli/commands/ai.ts
+++ b/apps/cli/commands/ai.ts
@@ -381,22 +381,26 @@ export async function runCommand(): Promise< void > {
 	ui.showWelcome();
 
 	let sessionRecorder: AiSessionRecorder | undefined;
-	let didDisableSessionPersistence = false;
+	let didDisableSessionPersistence = options.noSessionPersistence === true;
 	let sessionId: string | undefined = options.resumeSession?.summary.agentSessionId;
 
-	try {
-		if ( options.resumeSession ) {
-			sessionRecorder = await AiSessionRecorder.open( {
-				sessionId: options.resumeSession.summary.id,
-				filePath: options.resumeSession.summary.filePath,
-				linkedAgentSessionIds: options.resumeSession.summary.linkedAgentSessionIds,
-			} );
-		} else {
-			sessionRecorder = await AiSessionRecorder.create();
+	if ( options.noSessionPersistence ) {
+		ui.showInfo( 'Session persistence disabled (--no-session-persistence).' );
+	} else {
+		try {
+			if ( options.resumeSession ) {
+				sessionRecorder = await AiSessionRecorder.open( {
+					sessionId: options.resumeSession.summary.id,
+					filePath: options.resumeSession.summary.filePath,
+					linkedAgentSessionIds: options.resumeSession.summary.linkedAgentSessionIds,
+				} );
+			} else {
+				sessionRecorder = await AiSessionRecorder.create();
+			}
+		} catch ( error ) {
+			didDisableSessionPersistence = true;
+			ui.showError( `Session persistence disabled: ${ getErrorMessage( error ) }` );
 		}
-	} catch ( error ) {
-		didDisableSessionPersistence = true;
-		ui.showError( `Session persistence disabled: ${ getErrorMessage( error ) }` );
 	}
 
 	const persist = async ( callback: ( recorder: AiSessionRecorder ) => Promise< void > ) => {
@@ -718,6 +722,11 @@ export const registerCommand = ( yargs: StudioArgv ) => {
 				.option( 'path', {
 					hidden: true,
 				} )
+				.option( 'session-persistence', {
+					type: 'boolean',
+					default: true,
+					description: __( 'Record this AI chat session to disk' ),
+				} )
 				.command( {
 					command: 'sessions',
 					describe: __( 'Manage AI sessions' ),
@@ -759,8 +768,13 @@ export const registerCommand = ( yargs: StudioArgv ) => {
 								},
 								handler: async ( argv ) => {
 									try {
+										const noSessionPersistence =
+											( argv as { sessionPersistence?: boolean } ).sessionPersistence === false;
 										await runResumeSessionCommand(
-											typeof argv.id === 'string' ? argv.id : undefined
+											typeof argv.id === 'string' ? argv.id : undefined,
+											{
+												noSessionPersistence,
+											}
 										);
 									} catch ( error ) {
 										if ( error instanceof LoggerError ) {
@@ -806,9 +820,13 @@ export const registerCommand = ( yargs: StudioArgv ) => {
 					handler: async () => {},
 				} );
 		},
-		handler: async () => {
+		handler: async ( argv ) => {
 			try {
-				await runCommand();
+				const noSessionPersistence =
+					( argv as { sessionPersistence?: boolean } ).sessionPersistence === false;
+				await runCommand( {
+					noSessionPersistence,
+				} );
 			} catch ( error ) {
 				if ( error instanceof LoggerError ) {
 					logger.reportError( error );
diff --git a/apps/cli/commands/tests/ai.test.ts b/apps/cli/commands/tests/ai.test.ts
index d707e5984a..43899f9684 100644
--- a/apps/cli/commands/tests/ai.test.ts
+++ b/apps/cli/commands/tests/ai.test.ts
@@ -139,6 +139,19 @@ describe( 'CLI: studio ai sessions command', () => {
 		return parser;
 	}
 
+	it( 'records sessions by default when running studio ai', async () => {
+		await buildParser().parseAsync( [ 'ai' ] );
+
+		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).create ).toHaveBeenCalledTimes( 1 );
+	} );
+
+	it( 'disables session recording with --no-session-persistence', async () => {
+		await buildParser().parseAsync( [ 'ai', '--no-session-persistence' ] );
+
+		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).create ).not.toHaveBeenCalled();
+		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).open ).not.toHaveBeenCalled();
+	} );
+
 	it( 'resumes the latest session', async () => {
 		vi.mocked( listAiSessions ).mockResolvedValue( [
 			{
@@ -216,6 +229,42 @@ describe( 'CLI: studio ai sessions command', () => {
 		expect( console.log ).toHaveBeenCalledWith( expect.stringContaining( 'session-latest' ) );
 	} );
 
+	it( 'resumes latest without persistence when --no-session-persistence is set', async () => {
+		vi.mocked( listAiSessions ).mockResolvedValue( [
+			{
+				id: 'session-latest',
+				filePath: '/tmp/session-latest.jsonl',
+				createdAt: '2026-03-11T11:00:00.000Z',
+				updatedAt: '2026-03-11T11:00:00.000Z',
+				linkedAgentSessionIds: [],
+				eventCount: 1,
+			},
+		] );
+		vi.mocked( loadAiSession ).mockResolvedValue( {
+			summary: {
+				id: 'session-latest',
+				filePath: '/tmp/session-latest.jsonl',
+				createdAt: '2026-03-11T11:00:00.000Z',
+				updatedAt: '2026-03-11T11:00:00.000Z',
+				linkedAgentSessionIds: [],
+				eventCount: 1,
+			},
+			events: [],
+		} );
+
+		await buildParser().parseAsync( [
+			'ai',
+			'sessions',
+			'resume',
+			'latest',
+			'--no-session-persistence',
+		] );
+
+		expect( loadAiSession ).toHaveBeenCalledWith( 'session-latest' );
+		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).open ).not.toHaveBeenCalled();
+		expect( process.exit ).toHaveBeenCalledWith( 0 );
+	} );
+
 	it( 'reports an error when resuming latest and no sessions exist', async () => {
 		vi.mocked( listAiSessions ).mockResolvedValue( [] );
 

From be02222c5f035b17c5c15921d01b20dd218b92ff Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Thu, 12 Mar 2026 19:15:07 +0100
Subject: [PATCH 12/33] Move ai command to ai subfolder

---
 apps/cli/commands/{ai.ts => ai/index.ts} | 0
 1 file changed, 0 insertions(+), 0 deletions(-)
 rename apps/cli/commands/{ai.ts => ai/index.ts} (100%)

diff --git a/apps/cli/commands/ai.ts b/apps/cli/commands/ai/index.ts
similarity index 100%
rename from apps/cli/commands/ai.ts
rename to apps/cli/commands/ai/index.ts

From 425e67609d5b30ac8c6d44872bbd8868e2cb8baf Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Thu, 12 Mar 2026 19:29:08 +0100
Subject: [PATCH 13/33] Separate ai and ai sessions commands registration into
 separate files

---
 apps/cli/commands/ai/index.ts      | 316 +-----------------------
 apps/cli/commands/ai/sessions.ts   | 372 +++++++++++++++++++++++++++++
 apps/cli/commands/tests/ai.test.ts |  23 +-
 3 files changed, 394 insertions(+), 317 deletions(-)
 create mode 100644 apps/cli/commands/ai/sessions.ts

diff --git a/apps/cli/commands/ai/index.ts b/apps/cli/commands/ai/index.ts
index 703adff3c1..8af9647ee6 100644
--- a/apps/cli/commands/ai/index.ts
+++ b/apps/cli/commands/ai/index.ts
@@ -44,228 +44,6 @@ function getErrorMessage( error: unknown ): string {
 	return String( error );
 }
 
-function formatSessionTimestamp( timestamp: string ): string {
-	const parsed = Date.parse( timestamp );
-	if ( Number.isNaN( parsed ) ) {
-		return timestamp;
-	}
-
-	return new Date( parsed ).toISOString().replace( '.000Z', 'Z' ).replace( 'T', ' ' );
-}
-
-function getRelativeTime( timestamp: string ): string {
-	const targetMs = Date.parse( timestamp );
-	if ( Number.isNaN( targetMs ) ) {
-		return formatSessionTimestamp( timestamp );
-	}
-
-	const diffMs = targetMs - Date.now();
-	const absDiffMs = Math.abs( diffMs );
-	const rtf = new Intl.RelativeTimeFormat( undefined, { numeric: 'auto' } );
-	const units = [
-		{ unit: 'year', ms: 365 * 24 * 60 * 60 * 1000 },
-		{ unit: 'month', ms: 30 * 24 * 60 * 60 * 1000 },
-		{ unit: 'week', ms: 7 * 24 * 60 * 60 * 1000 },
-		{ unit: 'day', ms: 24 * 60 * 60 * 1000 },
-		{ unit: 'hour', ms: 60 * 60 * 1000 },
-		{ unit: 'minute', ms: 60 * 1000 },
-		{ unit: 'second', ms: 1000 },
-	] as const;
-
-	for ( const { unit, ms } of units ) {
-		if ( absDiffMs >= ms || unit === 'second' ) {
-			const value = Math.round( diffMs / ms );
-			return rtf.format( value, unit );
-		}
-	}
-
-	return formatSessionTimestamp( timestamp );
-}
-
-function toSingleLine( text: string ): string {
-	return text.replace( /\s+/g, ' ' ).trim();
-}
-
-function truncateWithEllipsis( text: string, maxLength: number ): string {
-	if ( text.length <= maxLength ) {
-		return text;
-	}
-
-	if ( maxLength <= 1 ) {
-		return '…';
-	}
-
-	return text.slice( 0, maxLength - 1 ) + '…';
-}
-
-function visibleWidth( text: string ): number {
-	return Array.from( text ).length;
-}
-
-function padEndVisible( text: string, width: number ): string {
-	return `${ text }${ ' '.repeat( Math.max( 0, width - visibleWidth( text ) ) ) }`;
-}
-
-function styleSessionId( id: string ): string {
-	return chalk.bold( id.slice( 0, 8 ) ) + chalk.dim( id.slice( 8 ) );
-}
-
-function formatSessionCompactLine(
-	session: AiSessionSummary,
-	terminalWidth: number,
-	layout: { idWidth: number; relativeWidth: number }
-): string {
-	const relative = getRelativeTime( session.updatedAt );
-	const prompt = toSingleLine( session.firstPrompt ?? __( '(No prompt yet)' ) );
-	const separator = chalk.dim( ' • ' );
-	const idText = padEndVisible( session.id, layout.idWidth );
-	const relativeText = padEndVisible( relative, layout.relativeWidth );
-	const hasStatusGlyph = session.endReason === 'error' || session.endReason === 'stopped';
-	const statusPlainWidth = hasStatusGlyph ? 2 : 0;
-	const siteLabelPlain = session.selectedSiteName ? `✻ ${ session.selectedSiteName }` : '';
-	const maxSiteLabelLength = Math.max( 8, Math.floor( terminalWidth * 0.25 ) );
-	const siteLabel = truncateWithEllipsis( siteLabelPlain, maxSiteLabelLength );
-	const suffixWidth = siteLabel ? visibleWidth( siteLabel ) : 0;
-	const gapWidth = siteLabel ? 2 : 0;
-	const prefixPlain = `${ idText } • ${ relativeText } • `;
-	const maxPromptLength = Math.max(
-		1,
-		terminalWidth - visibleWidth( prefixPlain ) - statusPlainWidth - gapWidth - suffixWidth - 1
-	);
-	const abstract = truncateWithEllipsis( prompt, maxPromptLength );
-	const promptStyled = session.firstPrompt ? chalk.white( abstract ) : chalk.dim( abstract );
-
-	const statusGlyph =
-		session.endReason === 'error'
-			? chalk.red( '✕ ' )
-			: session.endReason === 'stopped'
-			? chalk.gray( '◌ ' )
-			: '';
-	const leftPlain = `${ idText } • ${ relativeText } • ${ statusGlyph ? 'x ' : '' }${ abstract }`;
-	const renderedLeft = `${ styleSessionId( session.id ) }${ ' '.repeat(
-		Math.max( 0, layout.idWidth - visibleWidth( session.id ) )
-	) }${ separator }${ chalk.cyan( relative ) }${ ' '.repeat(
-		Math.max( 0, layout.relativeWidth - visibleWidth( relative ) )
-	) }${ separator }${ statusGlyph }${ promptStyled }`;
-	if ( ! siteLabel ) {
-		return renderedLeft;
-	}
-
-	const padding = Math.max(
-		2,
-		terminalWidth - visibleWidth( leftPlain ) - visibleWidth( siteLabel ) - 1
-	);
-	return `${ renderedLeft }${ ' '.repeat( padding ) }${ chalk.hex( '#8839ef' )( siteLabel ) }`;
-}
-
-function displaySessionsCompact( sessions: AiSessionSummary[] ): void {
-	const terminalWidth = Math.max( process.stdout.columns ?? 100, 60 );
-	const relativeTimes = sessions.map( ( session ) => getRelativeTime( session.updatedAt ) );
-	const layout = {
-		idWidth: Math.max( ...sessions.map( ( session ) => visibleWidth( session.id ) ) ),
-		relativeWidth: Math.max( ...relativeTimes.map( ( value ) => visibleWidth( value ) ) ),
-	};
-
-	console.log(
-		chalk.bold( __( 'AI Sessions' ) ) +
-			chalk.dim( ` (${ sessions.length })` ) +
-			chalk.dim( ` · ${ __( 'Most recent first' ) }` )
-	);
-
-	for ( const session of sessions ) {
-		console.log( formatSessionCompactLine( session, terminalWidth, layout ) );
-	}
-}
-
-async function runListSessionsCommand( format: 'compact' | 'json' ): Promise< void > {
-	const sessions = await listAiSessions();
-
-	if ( sessions.length === 0 ) {
-		console.log( __( 'No AI sessions found' ) );
-		return;
-	}
-
-	if ( format === 'json' ) {
-		console.log( JSON.stringify( sessions, null, 2 ) );
-		return;
-	}
-
-	displaySessionsCompact( sessions );
-}
-
-async function pickSessionInteractively(
-	sessions: AiSessionSummary[],
-	message: string
-): Promise< AiSessionSummary | undefined > {
-	const interactiveWidth = Math.max( ( process.stdout.columns ?? 100 ) - 4, 56 );
-	const abortController = new AbortController();
-	const handleEscKey = ( chunk: Buffer | string ) => {
-		const bytes = Buffer.isBuffer( chunk ) ? chunk : Buffer.from( chunk );
-		if ( bytes.length === 1 && bytes[ 0 ] === 0x1b ) {
-			abortController.abort();
-		}
-	};
-
-	if ( process.stdin.isTTY ) {
-		process.stdin.on( 'data', handleEscKey );
-	}
-
-	try {
-		const selectedSessionId = await select(
-			{
-				message,
-				choices: sessions.map( ( session ) => ( {
-					name: formatSessionCompactLine( session, interactiveWidth, {
-						idWidth: Math.max( ...sessions.map( ( s ) => visibleWidth( s.id ) ) ),
-						relativeWidth: Math.max(
-							...sessions.map( ( s ) => visibleWidth( getRelativeTime( s.updatedAt ) ) )
-						),
-					} ),
-					value: session.id,
-				} ) ),
-				pageSize: Math.min( 12, sessions.length ),
-				loop: false,
-				theme: {
-					style: {
-						keysHelpTip: () => chalk.dim( '↑↓ navigate · ⏎ select · esc cancel' ),
-					},
-				},
-			},
-			{
-				signal: abortController.signal,
-			}
-		);
-
-		return sessions.find( ( session ) => session.id === selectedSessionId );
-	} catch ( error ) {
-		if (
-			error instanceof Error &&
-			( error.name === 'AbortPromptError' || error.name === 'ExitPromptError' )
-		) {
-			return undefined;
-		}
-
-		throw error;
-	} finally {
-		if ( process.stdin.isTTY ) {
-			process.stdin.off( 'data', handleEscKey );
-		}
-	}
-}
-
-async function chooseSessionForAction(
-	actionLabel: string,
-	noSessionsMessage: string
-): Promise< AiSessionSummary | undefined > {
-	const sessions = await listAiSessions();
-	if ( sessions.length === 0 ) {
-		console.log( noSessionsMessage );
-		return undefined;
-	}
-
-	return pickSessionInteractively( sessions, actionLabel );
-}
-
 function extractAssistantMessageBlocks( message: SDKMessage ): AssistantMessageBlock[] {
 	if ( message.type !== 'assistant' ) {
 		return [];
@@ -715,7 +493,7 @@ export async function runCommand(): Promise< void > {
 
 export const registerCommand = ( yargs: StudioArgv ) => {
 	return yargs.command( {
-		command: 'ai',
+		command: '$0',
 		describe: __( 'AI-powered WordPress assistant' ),
 		builder: ( yargs ) => {
 			return yargs
@@ -726,98 +504,6 @@ export const registerCommand = ( yargs: StudioArgv ) => {
 					type: 'boolean',
 					default: true,
 					description: __( 'Record this AI chat session to disk' ),
-				} )
-				.command( {
-					command: 'sessions',
-					describe: __( 'Manage AI sessions' ),
-					builder: ( sessionsYargs ) => {
-						return sessionsYargs
-							.command( {
-								command: 'list',
-								describe: __( 'List AI sessions' ),
-								builder: ( listYargs ) => {
-									return listYargs.option( 'format', {
-										type: 'string',
-										choices: [ 'compact', 'json' ] as const,
-										default: 'compact' as const,
-										description: __( 'Output format' ),
-									} );
-								},
-								handler: async ( argv ) => {
-									try {
-										await runListSessionsCommand( argv.format as 'compact' | 'json' );
-									} catch ( error ) {
-										if ( error instanceof LoggerError ) {
-											logger.reportError( error );
-										} else {
-											logger.reportError(
-												new LoggerError( __( 'Failed to list AI sessions' ), error )
-											);
-										}
-									}
-								},
-							} )
-							.command( {
-								command: 'resume [id]',
-								describe: __( 'Resume an AI session (id, prefix, "latest", or picker)' ),
-								builder: ( resumeYargs ) => {
-									return resumeYargs.positional( 'id', {
-										type: 'string',
-										describe: __( 'Session id, id prefix, or "latest"' ),
-									} );
-								},
-								handler: async ( argv ) => {
-									try {
-										const noSessionPersistence =
-											( argv as { sessionPersistence?: boolean } ).sessionPersistence === false;
-										await runResumeSessionCommand(
-											typeof argv.id === 'string' ? argv.id : undefined,
-											{
-												noSessionPersistence,
-											}
-										);
-									} catch ( error ) {
-										if ( error instanceof LoggerError ) {
-											logger.reportError( error );
-										} else {
-											const loggerError = new LoggerError(
-												__( 'Failed to resume AI session' ),
-												error
-											);
-											logger.reportError( loggerError );
-										}
-									}
-								},
-							} )
-							.command( {
-								command: 'delete [id]',
-								describe: __( 'Delete an AI session (id, prefix, "latest", or picker)' ),
-								builder: ( deleteYargs ) => {
-									return deleteYargs.positional( 'id', {
-										type: 'string',
-										describe: __( 'Session id, id prefix, or "latest"' ),
-									} );
-								},
-								handler: async ( argv ) => {
-									try {
-										await runDeleteSessionCommand(
-											typeof argv.id === 'string' ? argv.id : undefined
-										);
-									} catch ( error ) {
-										if ( error instanceof LoggerError ) {
-											logger.reportError( error );
-										} else {
-											logger.reportError(
-												new LoggerError( __( 'Failed to delete AI session' ), error )
-											);
-										}
-									}
-								},
-							} )
-							.version( false )
-							.demandCommand( 1, __( 'You must provide a valid ai sessions command' ) );
-					},
-					handler: async () => {},
 				} );
 		},
 		handler: async ( argv ) => {
diff --git a/apps/cli/commands/ai/sessions.ts b/apps/cli/commands/ai/sessions.ts
new file mode 100644
index 0000000000..f1215bca9d
--- /dev/null
+++ b/apps/cli/commands/ai/sessions.ts
@@ -0,0 +1,372 @@
+import { select } from '@inquirer/prompts';
+import { __ } from '@wordpress/i18n';
+import chalk from 'chalk';
+import { runCommand as runAiCommand } from 'cli/commands/ai';
+import {
+	deleteAiSession,
+	listAiSessions,
+	loadAiSession,
+	type AiSessionSummary,
+} from 'cli/lib/ai-sessions';
+import { Logger, LoggerError } from 'cli/logger';
+import { StudioArgv } from 'cli/types';
+
+const logger = new Logger< string >();
+
+function formatSessionTimestamp( timestamp: string ): string {
+	const parsed = Date.parse( timestamp );
+	if ( Number.isNaN( parsed ) ) {
+		return timestamp;
+	}
+
+	return new Date( parsed ).toISOString().replace( '.000Z', 'Z' ).replace( 'T', ' ' );
+}
+
+function getRelativeTime( timestamp: string ): string {
+	const targetMs = Date.parse( timestamp );
+	if ( Number.isNaN( targetMs ) ) {
+		return formatSessionTimestamp( timestamp );
+	}
+
+	const diffMs = targetMs - Date.now();
+	const absDiffMs = Math.abs( diffMs );
+	const rtf = new Intl.RelativeTimeFormat( undefined, { numeric: 'auto' } );
+	const units = [
+		{ unit: 'year', ms: 365 * 24 * 60 * 60 * 1000 },
+		{ unit: 'month', ms: 30 * 24 * 60 * 60 * 1000 },
+		{ unit: 'week', ms: 7 * 24 * 60 * 60 * 1000 },
+		{ unit: 'day', ms: 24 * 60 * 60 * 1000 },
+		{ unit: 'hour', ms: 60 * 60 * 1000 },
+		{ unit: 'minute', ms: 60 * 1000 },
+		{ unit: 'second', ms: 1000 },
+	] as const;
+
+	for ( const { unit, ms } of units ) {
+		if ( absDiffMs >= ms || unit === 'second' ) {
+			const value = Math.round( diffMs / ms );
+			return rtf.format( value, unit );
+		}
+	}
+
+	return formatSessionTimestamp( timestamp );
+}
+
+function toSingleLine( text: string ): string {
+	return text.replace( /\s+/g, ' ' ).trim();
+}
+
+function truncateWithEllipsis( text: string, maxLength: number ): string {
+	if ( text.length <= maxLength ) {
+		return text;
+	}
+
+	if ( maxLength <= 1 ) {
+		return '…';
+	}
+
+	return text.slice( 0, maxLength - 1 ) + '…';
+}
+
+function visibleWidth( text: string ): number {
+	return Array.from( text ).length;
+}
+
+function padEndVisible( text: string, width: number ): string {
+	return `${ text }${ ' '.repeat( Math.max( 0, width - visibleWidth( text ) ) ) }`;
+}
+
+function styleSessionId( id: string ): string {
+	return chalk.bold( id.slice( 0, 8 ) ) + chalk.dim( id.slice( 8 ) );
+}
+
+function formatSessionCompactLine(
+	session: AiSessionSummary,
+	terminalWidth: number,
+	layout: { idWidth: number; relativeWidth: number }
+): string {
+	const relative = getRelativeTime( session.updatedAt );
+	const prompt = toSingleLine( session.firstPrompt ?? __( '(No prompt yet)' ) );
+	const separator = chalk.dim( ' • ' );
+	const idText = padEndVisible( session.id, layout.idWidth );
+	const relativeText = padEndVisible( relative, layout.relativeWidth );
+	const hasStatusGlyph = session.endReason === 'error' || session.endReason === 'stopped';
+	const statusPlainWidth = hasStatusGlyph ? 2 : 0;
+	const siteLabelPlain = session.selectedSiteName ? `✻ ${ session.selectedSiteName }` : '';
+	const maxSiteLabelLength = Math.max( 8, Math.floor( terminalWidth * 0.25 ) );
+	const siteLabel = truncateWithEllipsis( siteLabelPlain, maxSiteLabelLength );
+	const suffixWidth = siteLabel ? visibleWidth( siteLabel ) : 0;
+	const gapWidth = siteLabel ? 2 : 0;
+	const prefixPlain = `${ idText } • ${ relativeText } • `;
+	const maxPromptLength = Math.max(
+		1,
+		terminalWidth - visibleWidth( prefixPlain ) - statusPlainWidth - gapWidth - suffixWidth - 1
+	);
+	const abstract = truncateWithEllipsis( prompt, maxPromptLength );
+	const promptStyled = session.firstPrompt ? chalk.white( abstract ) : chalk.dim( abstract );
+
+	const statusGlyph =
+		session.endReason === 'error'
+			? chalk.red( '✕ ' )
+			: session.endReason === 'stopped'
+			? chalk.gray( '◌ ' )
+			: '';
+	const leftPlain = `${ idText } • ${ relativeText } • ${ statusGlyph ? 'x ' : '' }${ abstract }`;
+	const renderedLeft = `${ styleSessionId( session.id ) }${ ' '.repeat(
+		Math.max( 0, layout.idWidth - visibleWidth( session.id ) )
+	) }${ separator }${ chalk.cyan( relative ) }${ ' '.repeat(
+		Math.max( 0, layout.relativeWidth - visibleWidth( relative ) )
+	) }${ separator }${ statusGlyph }${ promptStyled }`;
+	if ( ! siteLabel ) {
+		return renderedLeft;
+	}
+
+	const padding = Math.max(
+		2,
+		terminalWidth - visibleWidth( leftPlain ) - visibleWidth( siteLabel ) - 1
+	);
+	return `${ renderedLeft }${ ' '.repeat( padding ) }${ chalk.hex( '#8839ef' )( siteLabel ) }`;
+}
+
+function displaySessionsCompact( sessions: AiSessionSummary[] ): void {
+	const terminalWidth = Math.max( process.stdout.columns ?? 100, 60 );
+	const relativeTimes = sessions.map( ( session ) => getRelativeTime( session.updatedAt ) );
+	const layout = {
+		idWidth: Math.max( ...sessions.map( ( session ) => visibleWidth( session.id ) ) ),
+		relativeWidth: Math.max( ...relativeTimes.map( ( value ) => visibleWidth( value ) ) ),
+	};
+
+	console.log(
+		chalk.bold( __( 'AI Sessions' ) ) +
+			chalk.dim( ` (${ sessions.length })` ) +
+			chalk.dim( ` · ${ __( 'Most recent first' ) }` )
+	);
+
+	for ( const session of sessions ) {
+		console.log( formatSessionCompactLine( session, terminalWidth, layout ) );
+	}
+}
+
+async function runListSessionsCommand( format: 'compact' | 'json' ): Promise< void > {
+	const sessions = await listAiSessions();
+
+	if ( sessions.length === 0 ) {
+		console.log( __( 'No AI sessions found' ) );
+		return;
+	}
+
+	if ( format === 'json' ) {
+		console.log( JSON.stringify( sessions, null, 2 ) );
+		return;
+	}
+
+	displaySessionsCompact( sessions );
+}
+
+async function pickSessionInteractively(
+	sessions: AiSessionSummary[],
+	message: string
+): Promise< AiSessionSummary | undefined > {
+	const interactiveWidth = Math.max( ( process.stdout.columns ?? 100 ) - 4, 56 );
+	const abortController = new AbortController();
+	const handleEscKey = ( chunk: Buffer | string ) => {
+		const bytes = Buffer.isBuffer( chunk ) ? chunk : Buffer.from( chunk );
+		if ( bytes.length === 1 && bytes[ 0 ] === 0x1b ) {
+			abortController.abort();
+		}
+	};
+
+	if ( process.stdin.isTTY ) {
+		process.stdin.on( 'data', handleEscKey );
+	}
+
+	try {
+		const selectedSessionId = await select(
+			{
+				message,
+				choices: sessions.map( ( session ) => ( {
+					name: formatSessionCompactLine( session, interactiveWidth, {
+						idWidth: Math.max( ...sessions.map( ( s ) => visibleWidth( s.id ) ) ),
+						relativeWidth: Math.max(
+							...sessions.map( ( s ) => visibleWidth( getRelativeTime( s.updatedAt ) ) )
+						),
+					} ),
+					value: session.id,
+				} ) ),
+				pageSize: Math.min( 12, sessions.length ),
+				loop: false,
+				theme: {
+					style: {
+						keysHelpTip: () => chalk.dim( '↑↓ navigate · ⏎ select · esc cancel' ),
+					},
+				},
+			},
+			{
+				signal: abortController.signal,
+			}
+		);
+
+		return sessions.find( ( session ) => session.id === selectedSessionId );
+	} catch ( error ) {
+		if (
+			error instanceof Error &&
+			( error.name === 'AbortPromptError' || error.name === 'ExitPromptError' )
+		) {
+			return undefined;
+		}
+
+		throw error;
+	} finally {
+		if ( process.stdin.isTTY ) {
+			process.stdin.off( 'data', handleEscKey );
+		}
+	}
+}
+
+async function chooseSessionForAction(
+	actionLabel: string,
+	noSessionsMessage: string
+): Promise< AiSessionSummary | undefined > {
+	const sessions = await listAiSessions();
+	if ( sessions.length === 0 ) {
+		console.log( noSessionsMessage );
+		return undefined;
+	}
+
+	return pickSessionInteractively( sessions, actionLabel );
+}
+
+async function runResumeSessionCommand(
+	sessionIdOrPrefix?: string,
+	options: { noSessionPersistence?: boolean } = {}
+): Promise< void > {
+	let resolvedSessionIdOrPrefix = sessionIdOrPrefix?.trim();
+
+	if ( ! resolvedSessionIdOrPrefix ) {
+		const selectedSession = await chooseSessionForAction(
+			__( 'Select a session to resume:' ),
+			__( 'No AI sessions found' )
+		);
+		if ( ! selectedSession ) {
+			return;
+		}
+
+		resolvedSessionIdOrPrefix = selectedSession.id;
+	}
+
+	if ( resolvedSessionIdOrPrefix.toLowerCase() === 'latest' ) {
+		const sessions = await listAiSessions();
+		if ( sessions.length === 0 ) {
+			throw new Error( __( 'No AI sessions found' ) );
+		}
+
+		resolvedSessionIdOrPrefix = sessions[ 0 ].id;
+	}
+
+	const session = await loadAiSession( resolvedSessionIdOrPrefix );
+	await runAiCommand( {
+		resumeSession: session,
+		noSessionPersistence: options.noSessionPersistence === true,
+	} );
+}
+
+async function runDeleteSessionCommand( sessionIdOrPrefix?: string ): Promise< void > {
+	let resolvedSessionIdOrPrefix = sessionIdOrPrefix?.trim();
+
+	if ( ! resolvedSessionIdOrPrefix ) {
+		const selectedSession = await chooseSessionForAction(
+			__( 'Select a session to delete:' ),
+			__( 'No AI sessions found' )
+		);
+		if ( ! selectedSession ) {
+			return;
+		}
+
+		resolvedSessionIdOrPrefix = selectedSession.id;
+	}
+
+	if ( resolvedSessionIdOrPrefix.toLowerCase() === 'latest' ) {
+		const sessions = await listAiSessions();
+		if ( sessions.length === 0 ) {
+			throw new Error( __( 'No AI sessions found' ) );
+		}
+
+		resolvedSessionIdOrPrefix = sessions[ 0 ].id;
+	}
+
+	const deletedSession = await deleteAiSession( resolvedSessionIdOrPrefix );
+	console.log( `${ __( 'Deleted AI session' ) }: ${ deletedSession.id }` );
+}
+
+export const registerCommand = ( yargs: StudioArgv ) => {
+	return yargs
+		.command( {
+			command: 'list',
+			describe: __( 'List AI sessions' ),
+			builder: ( listYargs ) => {
+				return listYargs.option( 'format', {
+					type: 'string',
+					choices: [ 'compact', 'json' ] as const,
+					default: 'compact' as const,
+					description: __( 'Output format' ),
+				} );
+			},
+			handler: async ( argv ) => {
+				try {
+					await runListSessionsCommand( argv.format as 'compact' | 'json' );
+				} catch ( error ) {
+					if ( error instanceof LoggerError ) {
+						logger.reportError( error );
+					} else {
+						logger.reportError( new LoggerError( __( 'Failed to list AI sessions' ), error ) );
+					}
+				}
+			},
+		} )
+		.command( {
+			command: 'resume [id]',
+			describe: __( 'Resume an AI session (id, prefix, "latest", or picker)' ),
+			builder: ( resumeYargs ) => {
+				return resumeYargs.positional( 'id', {
+					type: 'string',
+					describe: __( 'Session id, id prefix, or "latest"' ),
+				} );
+			},
+			handler: async ( argv ) => {
+				try {
+					const noSessionPersistence =
+						( argv as { sessionPersistence?: boolean } ).sessionPersistence === false;
+					await runResumeSessionCommand( typeof argv.id === 'string' ? argv.id : undefined, {
+						noSessionPersistence,
+					} );
+				} catch ( error ) {
+					if ( error instanceof LoggerError ) {
+						logger.reportError( error );
+					} else {
+						const loggerError = new LoggerError( __( 'Failed to resume AI session' ), error );
+						logger.reportError( loggerError );
+					}
+				}
+			},
+		} )
+		.command( {
+			command: 'delete [id]',
+			describe: __( 'Delete an AI session (id, prefix, "latest", or picker)' ),
+			builder: ( deleteYargs ) => {
+				return deleteYargs.positional( 'id', {
+					type: 'string',
+					describe: __( 'Session id, id prefix, or "latest"' ),
+				} );
+			},
+			handler: async ( argv ) => {
+				try {
+					await runDeleteSessionCommand( typeof argv.id === 'string' ? argv.id : undefined );
+				} catch ( error ) {
+					if ( error instanceof LoggerError ) {
+						logger.reportError( error );
+					} else {
+						logger.reportError( new LoggerError( __( 'Failed to delete AI session' ), error ) );
+					}
+				}
+			},
+		} );
+};
diff --git a/apps/cli/commands/tests/ai.test.ts b/apps/cli/commands/tests/ai.test.ts
index 43899f9684..bd30854d3b 100644
--- a/apps/cli/commands/tests/ai.test.ts
+++ b/apps/cli/commands/tests/ai.test.ts
@@ -1,6 +1,7 @@
 import { beforeEach, describe, expect, it, vi } from 'vitest';
 import yargs from 'yargs/yargs';
-import { registerCommand } from 'cli/commands/ai';
+import { registerCommand as registerAiCommand } from 'cli/commands/ai';
+import { registerCommand as registerAiSessionsCommand } from 'cli/commands/ai/sessions';
 import {
 	AiSessionRecorder,
 	deleteAiSession,
@@ -135,7 +136,25 @@ describe( 'CLI: studio ai sessions command', () => {
 
 	function buildParser(): StudioArgv {
 		const parser = yargs( [] ).scriptName( 'studio' ).strict().exitProcess( false ) as StudioArgv;
-		registerCommand( parser );
+		parser.command( 'ai', 'AI-powered WordPress assistant', ( aiYargs ) => {
+			registerAiCommand( aiYargs as StudioArgv );
+			aiYargs.command( 'sessions', 'Manage AI sessions', ( sessionsYargs ) => {
+				sessionsYargs
+					.option( 'path', {
+						hidden: true,
+					} )
+					.option( 'session-persistence', {
+						type: 'boolean',
+						default: true,
+						description: 'Record this AI chat session to disk',
+					} );
+				registerAiSessionsCommand( sessionsYargs as StudioArgv );
+				sessionsYargs
+					.version( false )
+					.demandCommand( 1, 'You must provide a valid ai sessions command' );
+			} );
+			aiYargs.version( false );
+		} );
 		return parser;
 	}
 

From 8aeb94619b04214af838b797bc5546492db835da Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Thu, 12 Mar 2026 19:33:18 +0100
Subject: [PATCH 14/33] Move sessions from lib to ai folder

---
 apps/cli/{lib/ai-sessions.ts => ai/sessions.ts} | 0
 apps/cli/commands/ai/sessions.ts                | 4 ++--
 apps/cli/commands/tests/ai.test.ts              | 9 ++-------
 apps/cli/lib/tests/ai-sessions.test.ts          | 2 +-
 4 files changed, 5 insertions(+), 10 deletions(-)
 rename apps/cli/{lib/ai-sessions.ts => ai/sessions.ts} (100%)

diff --git a/apps/cli/lib/ai-sessions.ts b/apps/cli/ai/sessions.ts
similarity index 100%
rename from apps/cli/lib/ai-sessions.ts
rename to apps/cli/ai/sessions.ts
diff --git a/apps/cli/commands/ai/sessions.ts b/apps/cli/commands/ai/sessions.ts
index f1215bca9d..19507a7963 100644
--- a/apps/cli/commands/ai/sessions.ts
+++ b/apps/cli/commands/ai/sessions.ts
@@ -1,13 +1,13 @@
 import { select } from '@inquirer/prompts';
 import { __ } from '@wordpress/i18n';
 import chalk from 'chalk';
-import { runCommand as runAiCommand } from 'cli/commands/ai';
 import {
 	deleteAiSession,
 	listAiSessions,
 	loadAiSession,
 	type AiSessionSummary,
-} from 'cli/lib/ai-sessions';
+} from 'cli/ai/sessions';
+import { runCommand as runAiCommand } from 'cli/commands/ai';
 import { Logger, LoggerError } from 'cli/logger';
 import { StudioArgv } from 'cli/types';
 
diff --git a/apps/cli/commands/tests/ai.test.ts b/apps/cli/commands/tests/ai.test.ts
index bd30854d3b..c918d622a3 100644
--- a/apps/cli/commands/tests/ai.test.ts
+++ b/apps/cli/commands/tests/ai.test.ts
@@ -1,13 +1,8 @@
 import { beforeEach, describe, expect, it, vi } from 'vitest';
 import yargs from 'yargs/yargs';
+import { AiSessionRecorder, deleteAiSession, listAiSessions, loadAiSession } from 'cli/ai/sessions';
 import { registerCommand as registerAiCommand } from 'cli/commands/ai';
 import { registerCommand as registerAiSessionsCommand } from 'cli/commands/ai/sessions';
-import {
-	AiSessionRecorder,
-	deleteAiSession,
-	listAiSessions,
-	loadAiSession,
-} from 'cli/lib/ai-sessions';
 import { getAnthropicApiKey } from 'cli/lib/appdata';
 import { StudioArgv } from 'cli/types';
 
@@ -105,7 +100,7 @@ vi.mock( 'cli/ai/ui', () => ( {
 		typeof input.detail === 'string' ? input.detail : '',
 } ) );
 
-vi.mock( 'cli/lib/ai-sessions', () => {
+vi.mock( 'cli/ai/sessions', () => {
 	class MockAiSessionRecorder {
 		static create = vi.fn().mockResolvedValue( new MockAiSessionRecorder() );
 		static open = vi.fn().mockResolvedValue( new MockAiSessionRecorder() );
diff --git a/apps/cli/lib/tests/ai-sessions.test.ts b/apps/cli/lib/tests/ai-sessions.test.ts
index 78f0955809..6468e5d20f 100644
--- a/apps/cli/lib/tests/ai-sessions.test.ts
+++ b/apps/cli/lib/tests/ai-sessions.test.ts
@@ -10,7 +10,7 @@ import {
 	loadAiSession,
 	listAiSessions,
 	readAiSessionEventsFromFile,
-} from 'cli/lib/ai-sessions';
+} from 'cli/ai/sessions';
 
 describe( 'ai-sessions', () => {
 	let testRoot: string | undefined;

From ec7b31a81314aa602e3d9f7e42cfda834e6028d4 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Thu, 12 Mar 2026 19:36:17 +0100
Subject: [PATCH 15/33] Move test files inside ai command tests folder

---
 apps/cli/commands/{ => ai}/tests/ai.test.ts                       | 0
 .../ai-sessions.test.ts => commands/ai/tests/sessions.test.ts}    | 0
 2 files changed, 0 insertions(+), 0 deletions(-)
 rename apps/cli/commands/{ => ai}/tests/ai.test.ts (100%)
 rename apps/cli/{lib/tests/ai-sessions.test.ts => commands/ai/tests/sessions.test.ts} (100%)

diff --git a/apps/cli/commands/tests/ai.test.ts b/apps/cli/commands/ai/tests/ai.test.ts
similarity index 100%
rename from apps/cli/commands/tests/ai.test.ts
rename to apps/cli/commands/ai/tests/ai.test.ts
diff --git a/apps/cli/lib/tests/ai-sessions.test.ts b/apps/cli/commands/ai/tests/sessions.test.ts
similarity index 100%
rename from apps/cli/lib/tests/ai-sessions.test.ts
rename to apps/cli/commands/ai/tests/sessions.test.ts

From f9174b7f3f9c0fe6283c38b5b645489042b11b33 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Thu, 12 Mar 2026 20:54:07 +0100
Subject: [PATCH 16/33] Separate sessions commands into separate files

---
 apps/cli/commands/ai/sessions/delete.ts       |  59 ++++++
 .../ai/{sessions.ts => sessions/helpers.ts}   | 168 +-----------------
 apps/cli/commands/ai/sessions/list.ts         |  51 ++++++
 apps/cli/commands/ai/sessions/resume.ts       |  71 ++++++++
 apps/cli/commands/ai/tests/ai.test.ts         |   8 +-
 5 files changed, 190 insertions(+), 167 deletions(-)
 create mode 100644 apps/cli/commands/ai/sessions/delete.ts
 rename apps/cli/commands/ai/{sessions.ts => sessions/helpers.ts} (58%)
 create mode 100644 apps/cli/commands/ai/sessions/list.ts
 create mode 100644 apps/cli/commands/ai/sessions/resume.ts

diff --git a/apps/cli/commands/ai/sessions/delete.ts b/apps/cli/commands/ai/sessions/delete.ts
new file mode 100644
index 0000000000..0aff012936
--- /dev/null
+++ b/apps/cli/commands/ai/sessions/delete.ts
@@ -0,0 +1,59 @@
+import { __ } from '@wordpress/i18n';
+import { deleteAiSession, listAiSessions } from 'cli/ai/sessions';
+import { chooseSessionForAction } from 'cli/commands/ai/sessions/helpers';
+import { Logger, LoggerError } from 'cli/logger';
+import { StudioArgv } from 'cli/types';
+
+const logger = new Logger< string >();
+
+export async function runCommand( sessionIdOrPrefix?: string ): Promise< void > {
+	let resolvedSessionIdOrPrefix = sessionIdOrPrefix?.trim();
+
+	if ( ! resolvedSessionIdOrPrefix ) {
+		const selectedSession = await chooseSessionForAction(
+			__( 'Select a session to delete:' ),
+			__( 'No AI sessions found' )
+		);
+		if ( ! selectedSession ) {
+			return;
+		}
+
+		resolvedSessionIdOrPrefix = selectedSession.id;
+	}
+
+	if ( resolvedSessionIdOrPrefix.toLowerCase() === 'latest' ) {
+		const sessions = await listAiSessions();
+		if ( sessions.length === 0 ) {
+			throw new Error( __( 'No AI sessions found' ) );
+		}
+
+		resolvedSessionIdOrPrefix = sessions[ 0 ].id;
+	}
+
+	const deletedSession = await deleteAiSession( resolvedSessionIdOrPrefix );
+	console.log( `${ __( 'Deleted AI session' ) }: ${ deletedSession.id }` );
+}
+
+export const registerCommand = ( yargs: StudioArgv ) => {
+	return yargs.command( {
+		command: 'delete [id]',
+		describe: __( 'Delete an AI session (id, prefix, "latest", or picker)' ),
+		builder: ( deleteYargs ) => {
+			return deleteYargs.positional( 'id', {
+				type: 'string',
+				describe: __( 'Session id, id prefix, or "latest"' ),
+			} );
+		},
+		handler: async ( argv ) => {
+			try {
+				await runCommand( typeof argv.id === 'string' ? argv.id : undefined );
+			} catch ( error ) {
+				if ( error instanceof LoggerError ) {
+					logger.reportError( error );
+				} else {
+					logger.reportError( new LoggerError( __( 'Failed to delete AI session' ), error ) );
+				}
+			}
+		},
+	} );
+};
diff --git a/apps/cli/commands/ai/sessions.ts b/apps/cli/commands/ai/sessions/helpers.ts
similarity index 58%
rename from apps/cli/commands/ai/sessions.ts
rename to apps/cli/commands/ai/sessions/helpers.ts
index 19507a7963..73a8281a7d 100644
--- a/apps/cli/commands/ai/sessions.ts
+++ b/apps/cli/commands/ai/sessions/helpers.ts
@@ -1,17 +1,7 @@
 import { select } from '@inquirer/prompts';
 import { __ } from '@wordpress/i18n';
 import chalk from 'chalk';
-import {
-	deleteAiSession,
-	listAiSessions,
-	loadAiSession,
-	type AiSessionSummary,
-} from 'cli/ai/sessions';
-import { runCommand as runAiCommand } from 'cli/commands/ai';
-import { Logger, LoggerError } from 'cli/logger';
-import { StudioArgv } from 'cli/types';
-
-const logger = new Logger< string >();
+import { listAiSessions, type AiSessionSummary } from 'cli/ai/sessions';
 
 function formatSessionTimestamp( timestamp: string ): string {
 	const parsed = Date.parse( timestamp );
@@ -127,7 +117,7 @@ function formatSessionCompactLine(
 	return `${ renderedLeft }${ ' '.repeat( padding ) }${ chalk.hex( '#8839ef' )( siteLabel ) }`;
 }
 
-function displaySessionsCompact( sessions: AiSessionSummary[] ): void {
+export function displaySessionsCompact( sessions: AiSessionSummary[] ): void {
 	const terminalWidth = Math.max( process.stdout.columns ?? 100, 60 );
 	const relativeTimes = sessions.map( ( session ) => getRelativeTime( session.updatedAt ) );
 	const layout = {
@@ -146,22 +136,6 @@ function displaySessionsCompact( sessions: AiSessionSummary[] ): void {
 	}
 }
 
-async function runListSessionsCommand( format: 'compact' | 'json' ): Promise< void > {
-	const sessions = await listAiSessions();
-
-	if ( sessions.length === 0 ) {
-		console.log( __( 'No AI sessions found' ) );
-		return;
-	}
-
-	if ( format === 'json' ) {
-		console.log( JSON.stringify( sessions, null, 2 ) );
-		return;
-	}
-
-	displaySessionsCompact( sessions );
-}
-
 async function pickSessionInteractively(
 	sessions: AiSessionSummary[],
 	message: string
@@ -222,7 +196,7 @@ async function pickSessionInteractively(
 	}
 }
 
-async function chooseSessionForAction(
+export async function chooseSessionForAction(
 	actionLabel: string,
 	noSessionsMessage: string
 ): Promise< AiSessionSummary | undefined > {
@@ -234,139 +208,3 @@ async function chooseSessionForAction(
 
 	return pickSessionInteractively( sessions, actionLabel );
 }
-
-async function runResumeSessionCommand(
-	sessionIdOrPrefix?: string,
-	options: { noSessionPersistence?: boolean } = {}
-): Promise< void > {
-	let resolvedSessionIdOrPrefix = sessionIdOrPrefix?.trim();
-
-	if ( ! resolvedSessionIdOrPrefix ) {
-		const selectedSession = await chooseSessionForAction(
-			__( 'Select a session to resume:' ),
-			__( 'No AI sessions found' )
-		);
-		if ( ! selectedSession ) {
-			return;
-		}
-
-		resolvedSessionIdOrPrefix = selectedSession.id;
-	}
-
-	if ( resolvedSessionIdOrPrefix.toLowerCase() === 'latest' ) {
-		const sessions = await listAiSessions();
-		if ( sessions.length === 0 ) {
-			throw new Error( __( 'No AI sessions found' ) );
-		}
-
-		resolvedSessionIdOrPrefix = sessions[ 0 ].id;
-	}
-
-	const session = await loadAiSession( resolvedSessionIdOrPrefix );
-	await runAiCommand( {
-		resumeSession: session,
-		noSessionPersistence: options.noSessionPersistence === true,
-	} );
-}
-
-async function runDeleteSessionCommand( sessionIdOrPrefix?: string ): Promise< void > {
-	let resolvedSessionIdOrPrefix = sessionIdOrPrefix?.trim();
-
-	if ( ! resolvedSessionIdOrPrefix ) {
-		const selectedSession = await chooseSessionForAction(
-			__( 'Select a session to delete:' ),
-			__( 'No AI sessions found' )
-		);
-		if ( ! selectedSession ) {
-			return;
-		}
-
-		resolvedSessionIdOrPrefix = selectedSession.id;
-	}
-
-	if ( resolvedSessionIdOrPrefix.toLowerCase() === 'latest' ) {
-		const sessions = await listAiSessions();
-		if ( sessions.length === 0 ) {
-			throw new Error( __( 'No AI sessions found' ) );
-		}
-
-		resolvedSessionIdOrPrefix = sessions[ 0 ].id;
-	}
-
-	const deletedSession = await deleteAiSession( resolvedSessionIdOrPrefix );
-	console.log( `${ __( 'Deleted AI session' ) }: ${ deletedSession.id }` );
-}
-
-export const registerCommand = ( yargs: StudioArgv ) => {
-	return yargs
-		.command( {
-			command: 'list',
-			describe: __( 'List AI sessions' ),
-			builder: ( listYargs ) => {
-				return listYargs.option( 'format', {
-					type: 'string',
-					choices: [ 'compact', 'json' ] as const,
-					default: 'compact' as const,
-					description: __( 'Output format' ),
-				} );
-			},
-			handler: async ( argv ) => {
-				try {
-					await runListSessionsCommand( argv.format as 'compact' | 'json' );
-				} catch ( error ) {
-					if ( error instanceof LoggerError ) {
-						logger.reportError( error );
-					} else {
-						logger.reportError( new LoggerError( __( 'Failed to list AI sessions' ), error ) );
-					}
-				}
-			},
-		} )
-		.command( {
-			command: 'resume [id]',
-			describe: __( 'Resume an AI session (id, prefix, "latest", or picker)' ),
-			builder: ( resumeYargs ) => {
-				return resumeYargs.positional( 'id', {
-					type: 'string',
-					describe: __( 'Session id, id prefix, or "latest"' ),
-				} );
-			},
-			handler: async ( argv ) => {
-				try {
-					const noSessionPersistence =
-						( argv as { sessionPersistence?: boolean } ).sessionPersistence === false;
-					await runResumeSessionCommand( typeof argv.id === 'string' ? argv.id : undefined, {
-						noSessionPersistence,
-					} );
-				} catch ( error ) {
-					if ( error instanceof LoggerError ) {
-						logger.reportError( error );
-					} else {
-						const loggerError = new LoggerError( __( 'Failed to resume AI session' ), error );
-						logger.reportError( loggerError );
-					}
-				}
-			},
-		} )
-		.command( {
-			command: 'delete [id]',
-			describe: __( 'Delete an AI session (id, prefix, "latest", or picker)' ),
-			builder: ( deleteYargs ) => {
-				return deleteYargs.positional( 'id', {
-					type: 'string',
-					describe: __( 'Session id, id prefix, or "latest"' ),
-				} );
-			},
-			handler: async ( argv ) => {
-				try {
-					await runDeleteSessionCommand( typeof argv.id === 'string' ? argv.id : undefined );
-				} catch ( error ) {
-					if ( error instanceof LoggerError ) {
-						logger.reportError( error );
-					} else {
-						logger.reportError( new LoggerError( __( 'Failed to delete AI session' ), error ) );
-					}
-				}
-			},
-		} );
-};
diff --git a/apps/cli/commands/ai/sessions/list.ts b/apps/cli/commands/ai/sessions/list.ts
new file mode 100644
index 0000000000..05ad7e8c1b
--- /dev/null
+++ b/apps/cli/commands/ai/sessions/list.ts
@@ -0,0 +1,51 @@
+import { __ } from '@wordpress/i18n';
+import { listAiSessions } from 'cli/ai/sessions';
+import { displaySessionsCompact } from 'cli/commands/ai/sessions/helpers';
+import { Logger, LoggerError } from 'cli/logger';
+import { StudioArgv } from 'cli/types';
+
+const logger = new Logger< string >();
+
+type SessionOutputFormat = 'compact' | 'json';
+
+export async function runCommand( format: SessionOutputFormat ): Promise< void > {
+	const sessions = await listAiSessions();
+
+	if ( sessions.length === 0 ) {
+		console.log( __( 'No AI sessions found' ) );
+		return;
+	}
+
+	if ( format === 'json' ) {
+		console.log( JSON.stringify( sessions, null, 2 ) );
+		return;
+	}
+
+	displaySessionsCompact( sessions );
+}
+
+export const registerCommand = ( yargs: StudioArgv ) => {
+	return yargs.command( {
+		command: 'list',
+		describe: __( 'List AI sessions' ),
+		builder: ( listYargs ) => {
+			return listYargs.option( 'format', {
+				type: 'string',
+				choices: [ 'compact', 'json' ] as const,
+				default: 'compact' as const,
+				description: __( 'Output format' ),
+			} );
+		},
+		handler: async ( argv ) => {
+			try {
+				await runCommand( argv.format as SessionOutputFormat );
+			} catch ( error ) {
+				if ( error instanceof LoggerError ) {
+					logger.reportError( error );
+				} else {
+					logger.reportError( new LoggerError( __( 'Failed to list AI sessions' ), error ) );
+				}
+			}
+		},
+	} );
+};
diff --git a/apps/cli/commands/ai/sessions/resume.ts b/apps/cli/commands/ai/sessions/resume.ts
new file mode 100644
index 0000000000..817b836e28
--- /dev/null
+++ b/apps/cli/commands/ai/sessions/resume.ts
@@ -0,0 +1,71 @@
+import { __ } from '@wordpress/i18n';
+import { listAiSessions, loadAiSession } from 'cli/ai/sessions';
+import { runCommand as runAiCommand } from 'cli/commands/ai';
+import { chooseSessionForAction } from 'cli/commands/ai/sessions/helpers';
+import { Logger, LoggerError } from 'cli/logger';
+import { StudioArgv } from 'cli/types';
+
+const logger = new Logger< string >();
+
+export async function runCommand(
+	sessionIdOrPrefix?: string,
+	options: { noSessionPersistence?: boolean } = {}
+): Promise< void > {
+	let resolvedSessionIdOrPrefix = sessionIdOrPrefix?.trim();
+
+	if ( ! resolvedSessionIdOrPrefix ) {
+		const selectedSession = await chooseSessionForAction(
+			__( 'Select a session to resume:' ),
+			__( 'No AI sessions found' )
+		);
+		if ( ! selectedSession ) {
+			return;
+		}
+
+		resolvedSessionIdOrPrefix = selectedSession.id;
+	}
+
+	if ( resolvedSessionIdOrPrefix.toLowerCase() === 'latest' ) {
+		const sessions = await listAiSessions();
+		if ( sessions.length === 0 ) {
+			throw new Error( __( 'No AI sessions found' ) );
+		}
+
+		resolvedSessionIdOrPrefix = sessions[ 0 ].id;
+	}
+
+	const session = await loadAiSession( resolvedSessionIdOrPrefix );
+	await runAiCommand( {
+		resumeSession: session,
+		noSessionPersistence: options.noSessionPersistence === true,
+	} );
+}
+
+export const registerCommand = ( yargs: StudioArgv ) => {
+	return yargs.command( {
+		command: 'resume [id]',
+		describe: __( 'Resume an AI session (id, prefix, "latest", or picker)' ),
+		builder: ( resumeYargs ) => {
+			return resumeYargs.positional( 'id', {
+				type: 'string',
+				describe: __( 'Session id, id prefix, or "latest"' ),
+			} );
+		},
+		handler: async ( argv ) => {
+			try {
+				const noSessionPersistence =
+					( argv as { sessionPersistence?: boolean } ).sessionPersistence === false;
+				await runCommand( typeof argv.id === 'string' ? argv.id : undefined, {
+					noSessionPersistence,
+				} );
+			} catch ( error ) {
+				if ( error instanceof LoggerError ) {
+					logger.reportError( error );
+				} else {
+					const loggerError = new LoggerError( __( 'Failed to resume AI session' ), error );
+					logger.reportError( loggerError );
+				}
+			}
+		},
+	} );
+};
diff --git a/apps/cli/commands/ai/tests/ai.test.ts b/apps/cli/commands/ai/tests/ai.test.ts
index c918d622a3..013012b587 100644
--- a/apps/cli/commands/ai/tests/ai.test.ts
+++ b/apps/cli/commands/ai/tests/ai.test.ts
@@ -2,7 +2,9 @@ import { beforeEach, describe, expect, it, vi } from 'vitest';
 import yargs from 'yargs/yargs';
 import { AiSessionRecorder, deleteAiSession, listAiSessions, loadAiSession } from 'cli/ai/sessions';
 import { registerCommand as registerAiCommand } from 'cli/commands/ai';
-import { registerCommand as registerAiSessionsCommand } from 'cli/commands/ai/sessions';
+import { registerCommand as registerAiSessionsDeleteCommand } from 'cli/commands/ai/sessions/delete';
+import { registerCommand as registerAiSessionsListCommand } from 'cli/commands/ai/sessions/list';
+import { registerCommand as registerAiSessionsResumeCommand } from 'cli/commands/ai/sessions/resume';
 import { getAnthropicApiKey } from 'cli/lib/appdata';
 import { StudioArgv } from 'cli/types';
 
@@ -143,7 +145,9 @@ describe( 'CLI: studio ai sessions command', () => {
 						default: true,
 						description: 'Record this AI chat session to disk',
 					} );
-				registerAiSessionsCommand( sessionsYargs as StudioArgv );
+				registerAiSessionsListCommand( sessionsYargs as StudioArgv );
+				registerAiSessionsResumeCommand( sessionsYargs as StudioArgv );
+				registerAiSessionsDeleteCommand( sessionsYargs as StudioArgv );
 				sessionsYargs
 					.version( false )
 					.demandCommand( 1, 'You must provide a valid ai sessions command' );

From 322a835718119694170685c84ed4ea268930007c Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Thu, 12 Mar 2026 21:19:30 +0100
Subject: [PATCH 17/33] Separate sessions into submodules

---
 apps/cli/ai/sessions.ts                     | 486 --------------------
 apps/cli/ai/sessions/parser.ts              | 166 +++++++
 apps/cli/ai/sessions/paths.ts               |  17 +
 apps/cli/ai/sessions/recorder.ts            | 160 +++++++
 apps/cli/ai/sessions/replay.ts              |  65 +++
 apps/cli/ai/sessions/store.ts               | 140 ++++++
 apps/cli/ai/sessions/summary.ts             |  80 ++++
 apps/cli/ai/sessions/types.ts               |  86 ++++
 apps/cli/commands/ai/index.ts               |   3 +-
 apps/cli/commands/ai/sessions/delete.ts     |   2 +-
 apps/cli/commands/ai/sessions/helpers.ts    |   3 +-
 apps/cli/commands/ai/sessions/list.ts       |   2 +-
 apps/cli/commands/ai/sessions/resume.ts     |   2 +-
 apps/cli/commands/ai/tests/ai.test.ts       |  32 +-
 apps/cli/commands/ai/tests/sessions.test.ts |   9 +-
 15 files changed, 747 insertions(+), 506 deletions(-)
 delete mode 100644 apps/cli/ai/sessions.ts
 create mode 100644 apps/cli/ai/sessions/parser.ts
 create mode 100644 apps/cli/ai/sessions/paths.ts
 create mode 100644 apps/cli/ai/sessions/recorder.ts
 create mode 100644 apps/cli/ai/sessions/replay.ts
 create mode 100644 apps/cli/ai/sessions/store.ts
 create mode 100644 apps/cli/ai/sessions/summary.ts
 create mode 100644 apps/cli/ai/sessions/types.ts

diff --git a/apps/cli/ai/sessions.ts b/apps/cli/ai/sessions.ts
deleted file mode 100644
index 8dbde331d5..0000000000
--- a/apps/cli/ai/sessions.ts
+++ /dev/null
@@ -1,486 +0,0 @@
-import crypto from 'crypto';
-import fs from 'fs/promises';
-import path from 'path';
-import { getAppdataDirectory } from 'cli/lib/appdata';
-
-export type TurnStatus = 'success' | 'error' | 'max_turns' | 'interrupted';
-
-export type AssistantMessageBlock =
-	| {
-			type: 'text';
-			text: string;
-	  }
-	| {
-			type: 'tool_use';
-			name: string;
-			detail?: string;
-	  };
-
-export type AiSessionEvent =
-	| {
-			type: 'session.started';
-			timestamp: string;
-			version: 1;
-			sessionId: string;
-	  }
-	| {
-			type: 'session.linked';
-			timestamp: string;
-			agentSessionId: string;
-	  }
-	| {
-			type: 'site.selected';
-			timestamp: string;
-			siteName: string;
-			sitePath: string;
-	  }
-	| {
-			type: 'user.message';
-			timestamp: string;
-			text: string;
-			source: 'prompt' | 'ask_user';
-			sitePath?: string;
-	  }
-	| {
-			type: 'assistant.message';
-			timestamp: string;
-			blocks: AssistantMessageBlock[];
-	  }
-	| {
-			type: 'tool.result';
-			timestamp: string;
-			ok: boolean;
-			text: string;
-	  }
-	| {
-			type: 'tool.progress';
-			timestamp: string;
-			message: string;
-	  }
-	| {
-			type: 'agent.question';
-			timestamp: string;
-			question: string;
-			options: Array< {
-				label: string;
-				description: string;
-			} >;
-	  }
-	| {
-			type: 'turn.closed';
-			timestamp: string;
-			status: TurnStatus;
-	  };
-
-export interface AiSessionSummary {
-	id: string;
-	filePath: string;
-	createdAt: string;
-	updatedAt: string;
-	agentSessionId?: string;
-	linkedAgentSessionIds: string[];
-	firstPrompt?: string;
-	selectedSiteName?: string;
-	endReason?: 'error' | 'stopped';
-	eventCount: number;
-}
-
-export interface LoadedAiSession {
-	summary: AiSessionSummary;
-	events: AiSessionEvent[];
-}
-
-export function getAiSessionsRootDirectory(): string {
-	return path.join( getAppdataDirectory(), 'sessions' );
-}
-
-function formatDatePart( value: number ): string {
-	return String( value ).padStart( 2, '0' );
-}
-
-function toSortableTimestampPrefix( date: Date ): string {
-	return date
-		.toISOString()
-		.replace( /:/g, '-' )
-		.replace( /\.\d{3}Z$/, '' );
-}
-
-export function getAiSessionsDirectoryForDate( date: Date ): string {
-	const year = String( date.getFullYear() );
-	const month = formatDatePart( date.getMonth() + 1 );
-	const day = formatDatePart( date.getDate() );
-	return path.join( getAiSessionsRootDirectory(), year, month, day );
-}
-
-function toIsoTimestamp( value?: Date ): string {
-	return ( value ?? new Date() ).toISOString();
-}
-
-export class AiSessionRecorder {
-	public readonly sessionId: string;
-	public readonly filePath: string;
-
-	private linkedAgentSessionIds = new Set< string >();
-
-	private constructor( sessionId: string, filePath: string, linkedAgentSessionIds: string[] = [] ) {
-		this.sessionId = sessionId;
-		this.filePath = filePath;
-		this.linkedAgentSessionIds = new Set( linkedAgentSessionIds );
-	}
-
-	static async create( options: { startedAt?: Date } = {} ): Promise< AiSessionRecorder > {
-		const startedAt = options.startedAt ?? new Date();
-		const sessionId = crypto.randomUUID();
-		const directory = getAiSessionsDirectoryForDate( startedAt );
-		const fileName = `${ toSortableTimestampPrefix( startedAt ) }-${ sessionId }.jsonl`;
-		const filePath = path.join( directory, fileName );
-
-		await fs.mkdir( directory, { recursive: true } );
-
-		const recorder = new AiSessionRecorder( sessionId, filePath );
-		await recorder.appendEvent( {
-			type: 'session.started',
-			timestamp: toIsoTimestamp( startedAt ),
-			version: 1,
-			sessionId,
-		} );
-
-		return recorder;
-	}
-
-	static async open( options: {
-		sessionId: string;
-		filePath: string;
-		linkedAgentSessionIds?: string[];
-	} ): Promise< AiSessionRecorder > {
-		await fs.access( options.filePath );
-		return new AiSessionRecorder(
-			options.sessionId,
-			options.filePath,
-			options.linkedAgentSessionIds ?? []
-		);
-	}
-
-	async recordAgentSessionId( agentSessionId: string ): Promise< void > {
-		if ( this.linkedAgentSessionIds.has( agentSessionId ) ) {
-			return;
-		}
-
-		this.linkedAgentSessionIds.add( agentSessionId );
-		await this.appendEvent( {
-			type: 'session.linked',
-			timestamp: toIsoTimestamp(),
-			agentSessionId,
-		} );
-	}
-
-	async recordSiteSelected( site: { name: string; path: string } ): Promise< void > {
-		await this.appendEvent( {
-			type: 'site.selected',
-			timestamp: toIsoTimestamp(),
-			siteName: site.name,
-			sitePath: site.path,
-		} );
-	}
-
-	async recordUserMessage( options: {
-		text: string;
-		source: 'prompt' | 'ask_user';
-		sitePath?: string;
-	} ): Promise< void > {
-		await this.appendEvent( {
-			type: 'user.message',
-			timestamp: toIsoTimestamp(),
-			text: options.text,
-			source: options.source,
-			sitePath: options.sitePath,
-		} );
-	}
-
-	async recordAssistantMessage( blocks: AssistantMessageBlock[] ): Promise< void > {
-		if ( blocks.length === 0 ) {
-			return;
-		}
-
-		await this.appendEvent( {
-			type: 'assistant.message',
-			timestamp: toIsoTimestamp(),
-			blocks,
-		} );
-	}
-
-	async recordToolResult( options: { ok: boolean; text: string } ): Promise< void > {
-		await this.appendEvent( {
-			type: 'tool.result',
-			timestamp: toIsoTimestamp(),
-			ok: options.ok,
-			text: options.text,
-		} );
-	}
-
-	async recordToolProgress( message: string ): Promise< void > {
-		if ( ! message.trim() ) {
-			return;
-		}
-
-		await this.appendEvent( {
-			type: 'tool.progress',
-			timestamp: toIsoTimestamp(),
-			message,
-		} );
-	}
-
-	async recordAgentQuestion( options: {
-		question: string;
-		options: Array< {
-			label: string;
-			description: string;
-		} >;
-	} ): Promise< void > {
-		await this.appendEvent( {
-			type: 'agent.question',
-			timestamp: toIsoTimestamp(),
-			question: options.question,
-			options: options.options,
-		} );
-	}
-
-	async recordTurnClosed( status: TurnStatus ): Promise< void > {
-		await this.appendEvent( {
-			type: 'turn.closed',
-			timestamp: toIsoTimestamp(),
-			status,
-		} );
-	}
-
-	private async appendEvent( event: AiSessionEvent ): Promise< void > {
-		await fs.appendFile( this.filePath, `${ JSON.stringify( event ) }\n`, {
-			encoding: 'utf8',
-		} );
-	}
-}
-
-export async function readAiSessionEventsFromFile( filePath: string ): Promise< AiSessionEvent[] > {
-	const content = await fs.readFile( filePath, 'utf8' );
-	const lines = content
-		.split( '\n' )
-		.map( ( line ) => line.trim() )
-		.filter( ( line ) => line.length > 0 );
-	const events: AiSessionEvent[] = [];
-
-	for ( const line of lines ) {
-		try {
-			events.push( JSON.parse( line ) as AiSessionEvent );
-		} catch {
-			// Ignore malformed lines and keep loading the rest.
-		}
-	}
-
-	return events;
-}
-
-function getSessionIdFromPath( filePath: string ): string {
-	const fileName = path.basename( filePath, '.jsonl' );
-	const uuidMatch = fileName.match(
-		/\b([0-9a-f]{8}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{12})\b/i
-	);
-	return uuidMatch?.[ 1 ] ?? fileName;
-}
-
-async function listSessionFilesRecursively( directory: string ): Promise< string[] > {
-	try {
-		const entries = await fs.readdir( directory, { withFileTypes: true, encoding: 'utf8' } );
-
-		const nestedFiles = await Promise.all(
-			entries.map( async ( entry ) => {
-				const fullPath = path.join( directory, entry.name );
-
-				if ( entry.isDirectory() ) {
-					return listSessionFilesRecursively( fullPath );
-				}
-
-				if ( entry.isFile() && entry.name.endsWith( '.jsonl' ) ) {
-					return [ fullPath ];
-				}
-
-				return [];
-			} )
-		);
-
-		return nestedFiles.flat();
-	} catch ( error ) {
-		const fsError = error as NodeJS.ErrnoException;
-		if ( fsError.code === 'ENOENT' ) {
-			return [];
-		}
-
-		throw error;
-	}
-}
-
-async function readAiSessionSummaryFromFile(
-	filePath: string
-): Promise< AiSessionSummary | undefined > {
-	const events = await readAiSessionEventsFromFile( filePath );
-	if ( events.length === 0 ) {
-		return undefined;
-	}
-
-	const linkedAgentSessionIds: string[] = [];
-	let createdAt: string | undefined;
-	let updatedAt: string | undefined;
-	let sessionId = getSessionIdFromPath( filePath );
-	let firstPrompt: string | undefined;
-	let selectedSiteName: string | undefined;
-	let endReason: 'error' | 'stopped' | undefined;
-	let eventCount = 0;
-
-	for ( const event of events ) {
-		eventCount += 1;
-		updatedAt = event.timestamp;
-
-		if ( event.type === 'session.started' ) {
-			createdAt = event.timestamp;
-			if ( event.sessionId.trim().length > 0 ) {
-				sessionId = event.sessionId;
-			}
-		}
-
-		if (
-			event.type === 'session.linked' &&
-			! linkedAgentSessionIds.includes( event.agentSessionId )
-		) {
-			linkedAgentSessionIds.push( event.agentSessionId );
-		}
-
-		if ( event.type === 'site.selected' ) {
-			selectedSiteName = event.siteName;
-		}
-
-		if ( event.type === 'user.message' && event.source === 'prompt' && ! firstPrompt ) {
-			firstPrompt = event.text;
-		}
-
-		if ( event.type === 'turn.closed' ) {
-			if ( event.status === 'error' ) {
-				endReason = 'error';
-			} else if ( event.status === 'interrupted' ) {
-				endReason = 'stopped';
-			}
-		}
-	}
-
-	const stats = await fs.stat( filePath );
-	const fallbackTimestamp = stats.mtime.toISOString();
-
-	return {
-		id: sessionId,
-		filePath,
-		createdAt: createdAt ?? fallbackTimestamp,
-		updatedAt: updatedAt ?? createdAt ?? fallbackTimestamp,
-		agentSessionId: linkedAgentSessionIds[ linkedAgentSessionIds.length - 1 ],
-		linkedAgentSessionIds,
-		firstPrompt,
-		selectedSiteName,
-		endReason,
-		eventCount,
-	};
-}
-
-export async function listAiSessions(): Promise< AiSessionSummary[] > {
-	const sessionFiles = await listSessionFilesRecursively( getAiSessionsRootDirectory() );
-	const results = await Promise.allSettled(
-		sessionFiles.map( ( filePath ) => readAiSessionSummaryFromFile( filePath ) )
-	);
-
-	const sessions = results
-		.filter(
-			( result ): result is PromiseFulfilledResult< AiSessionSummary | undefined > =>
-				result.status === 'fulfilled'
-		)
-		.map( ( result ) => result.value )
-		.filter( ( session ): session is AiSessionSummary => !! session );
-
-	return sessions.sort( ( a, b ) => Date.parse( b.updatedAt ) - Date.parse( a.updatedAt ) );
-}
-
-export async function loadAiSession( sessionIdOrPrefix: string ): Promise< LoadedAiSession > {
-	const sessions = await listAiSessions();
-	const exactMatch = sessions.find( ( session ) => session.id === sessionIdOrPrefix );
-	const candidates = exactMatch
-		? [ exactMatch ]
-		: sessions.filter( ( session ) => session.id.startsWith( sessionIdOrPrefix ) );
-
-	if ( candidates.length === 0 ) {
-		throw new Error( `AI session not found: ${ sessionIdOrPrefix }` );
-	}
-
-	if ( candidates.length > 1 ) {
-		const sample = candidates
-			.slice( 0, 5 )
-			.map( ( session ) => session.id )
-			.join( ', ' );
-		throw new Error(
-			`Session id prefix is ambiguous: ${ sessionIdOrPrefix }. Matches: ${ sample }${
-				candidates.length > 5 ? ', …' : ''
-			}`
-		);
-	}
-
-	const summary = candidates[ 0 ];
-	const events = await readAiSessionEventsFromFile( summary.filePath );
-	return { summary, events };
-}
-
-async function pruneEmptySessionDirectories( startDirectory: string ): Promise< void > {
-	const rootDirectory = getAiSessionsRootDirectory();
-	let currentDirectory = startDirectory;
-
-	while (
-		currentDirectory.startsWith( rootDirectory + path.sep ) &&
-		currentDirectory !== rootDirectory
-	) {
-		try {
-			await fs.rmdir( currentDirectory );
-		} catch ( error ) {
-			const fsError = error as NodeJS.ErrnoException;
-			if ( fsError.code === 'ENOTEMPTY' || fsError.code === 'ENOENT' ) {
-				return;
-			}
-
-			throw error;
-		}
-
-		currentDirectory = path.dirname( currentDirectory );
-	}
-}
-
-export async function deleteAiSession( sessionIdOrPrefix: string ): Promise< AiSessionSummary > {
-	const sessions = await listAiSessions();
-	const exactMatch = sessions.find( ( session ) => session.id === sessionIdOrPrefix );
-	const candidates = exactMatch
-		? [ exactMatch ]
-		: sessions.filter( ( session ) => session.id.startsWith( sessionIdOrPrefix ) );
-
-	if ( candidates.length === 0 ) {
-		throw new Error( `AI session not found: ${ sessionIdOrPrefix }` );
-	}
-
-	if ( candidates.length > 1 ) {
-		const sample = candidates
-			.slice( 0, 5 )
-			.map( ( session ) => session.id )
-			.join( ', ' );
-		throw new Error(
-			`Session id prefix is ambiguous: ${ sessionIdOrPrefix }. Matches: ${ sample }${
-				candidates.length > 5 ? ', …' : ''
-			}`
-		);
-	}
-
-	const sessionToDelete = candidates[ 0 ];
-	await fs.rm( sessionToDelete.filePath, { force: false } );
-	await pruneEmptySessionDirectories( path.dirname( sessionToDelete.filePath ) );
-
-	return sessionToDelete;
-}
diff --git a/apps/cli/ai/sessions/parser.ts b/apps/cli/ai/sessions/parser.ts
new file mode 100644
index 0000000000..e7d23f1493
--- /dev/null
+++ b/apps/cli/ai/sessions/parser.ts
@@ -0,0 +1,166 @@
+import type { AssistantMessageBlock } from './types';
+import type { SDKMessage } from '@anthropic-ai/claude-agent-sdk';
+
+type ToolDetailResolver = ( name: string, input: Record< string, unknown > ) => string;
+
+export function extractAssistantMessageBlocks(
+	message: SDKMessage,
+	resolveToolDetail: ToolDetailResolver
+): AssistantMessageBlock[] {
+	if ( message.type !== 'assistant' ) {
+		return [];
+	}
+
+	const blocks: AssistantMessageBlock[] = [];
+	for ( const block of message.message.content ) {
+		if ( block.type === 'text' && block.text ) {
+			blocks.push( {
+				type: 'text',
+				text: block.text,
+			} );
+		}
+
+		if ( block.type === 'tool_use' && block.name ) {
+			const detail =
+				block.input && typeof block.input === 'object'
+					? resolveToolDetail( block.name, block.input as Record< string, unknown > )
+					: '';
+			blocks.push( {
+				type: 'tool_use',
+				name: block.name,
+				detail: detail || undefined,
+			} );
+		}
+	}
+
+	return blocks;
+}
+
+function toToolResultText( value: unknown ): string {
+	if ( Array.isArray( value ) ) {
+		const lines = value
+			.map( ( item ) => {
+				if ( typeof item === 'string' ) {
+					return item;
+				}
+
+				if ( item && typeof item === 'object' ) {
+					const typedItem = item as { type?: unknown; text?: unknown };
+					if ( typedItem.type === 'text' && typeof typedItem.text === 'string' ) {
+						return typedItem.text;
+					}
+
+					try {
+						return JSON.stringify( item, null, 2 );
+					} catch {
+						return String( item );
+					}
+				}
+
+				return String( item );
+			} )
+			.map( ( line ) => line.trim() )
+			.filter( ( line ) => line.length > 0 );
+
+		return lines.join( '\n' );
+	}
+
+	if ( typeof value === 'string' ) {
+		return value.trim();
+	}
+
+	if ( value === null || value === undefined ) {
+		return '';
+	}
+
+	try {
+		return JSON.stringify( value, null, 2 );
+	} catch {
+		return String( value );
+	}
+}
+
+export function extractToolResult(
+	message: SDKMessage
+): { ok: boolean; text: string } | undefined {
+	if ( message.type !== 'user' ) {
+		return undefined;
+	}
+
+	const rawResult = message.tool_use_result;
+	if ( ! rawResult ) {
+		return undefined;
+	}
+
+	if ( typeof rawResult !== 'object' ) {
+		const text = String( rawResult ).trim();
+		return {
+			ok: true,
+			text,
+		};
+	}
+
+	const typedResult = rawResult as {
+		content?: unknown;
+		isError?: unknown;
+		is_error?: unknown;
+	};
+	const isError = typedResult.isError === true || typedResult.is_error === true;
+	const textFromContent = toToolResultText( typedResult.content );
+
+	return {
+		ok: ! isError,
+		text: textFromContent,
+	};
+}
+
+function toReplayToolInput( _name: string, detail?: string ): Record< string, unknown > {
+	if ( ! detail ) {
+		return {};
+	}
+
+	return { detail };
+}
+
+export function toReplayAssistantMessage( blocks: AssistantMessageBlock[] ): SDKMessage {
+	return {
+		type: 'assistant',
+		message: {
+			content: blocks.map( ( block, index ) => {
+				if ( block.type === 'text' ) {
+					return {
+						type: 'text',
+						text: block.text,
+					};
+				}
+
+				return {
+					type: 'tool_use',
+					id: `replay-tool-${ index }`,
+					name: block.name,
+					input: toReplayToolInput( block.name, block.detail ),
+				};
+			} ),
+		},
+	} as SDKMessage;
+}
+
+export function toReplayToolResultMessage( options: { ok: boolean; text: string } ): SDKMessage {
+	const normalizedText = options.text.trim();
+	const content = ! normalizedText
+		? []
+		: [
+				{
+					type: 'text',
+					text: options.text,
+				},
+		  ];
+
+	return {
+		type: 'user',
+		tool_use_result: {
+			isError: ! options.ok,
+			content,
+		},
+	} as SDKMessage;
+}
diff --git a/apps/cli/ai/sessions/paths.ts b/apps/cli/ai/sessions/paths.ts
new file mode 100644
index 0000000000..da69fb1796
--- /dev/null
+++ b/apps/cli/ai/sessions/paths.ts
@@ -0,0 +1,17 @@
+import path from 'path';
+import { getAppdataDirectory } from 'cli/lib/appdata';
+
+function formatDatePart( value: number ): string {
+	return String( value ).padStart( 2, '0' );
+}
+
+export function getAiSessionsRootDirectory(): string {
+	return path.join( getAppdataDirectory(), 'sessions' );
+}
+
+export function getAiSessionsDirectoryForDate( date: Date ): string {
+	const year = String( date.getFullYear() );
+	const month = formatDatePart( date.getMonth() + 1 );
+	const day = formatDatePart( date.getDate() );
+	return path.join( getAiSessionsRootDirectory(), year, month, day );
+}
diff --git a/apps/cli/ai/sessions/recorder.ts b/apps/cli/ai/sessions/recorder.ts
new file mode 100644
index 0000000000..14fdcfde48
--- /dev/null
+++ b/apps/cli/ai/sessions/recorder.ts
@@ -0,0 +1,160 @@
+import crypto from 'crypto';
+import fs from 'fs/promises';
+import path from 'path';
+import { getAiSessionsDirectoryForDate } from './paths';
+import type { AiSessionEvent, AssistantMessageBlock, TurnStatus } from './types';
+
+function toSortableTimestampPrefix( date: Date ): string {
+	return date
+		.toISOString()
+		.replace( /:/g, '-' )
+		.replace( /\.\d{3}Z$/, '' );
+}
+
+function toIsoTimestamp( value?: Date ): string {
+	return ( value ?? new Date() ).toISOString();
+}
+
+export class AiSessionRecorder {
+	public readonly sessionId: string;
+	public readonly filePath: string;
+
+	private linkedAgentSessionIds = new Set< string >();
+
+	private constructor( sessionId: string, filePath: string, linkedAgentSessionIds: string[] = [] ) {
+		this.sessionId = sessionId;
+		this.filePath = filePath;
+		this.linkedAgentSessionIds = new Set( linkedAgentSessionIds );
+	}
+
+	static async create( options: { startedAt?: Date } = {} ): Promise< AiSessionRecorder > {
+		const startedAt = options.startedAt ?? new Date();
+		const sessionId = crypto.randomUUID();
+		const directory = getAiSessionsDirectoryForDate( startedAt );
+		const fileName = `${ toSortableTimestampPrefix( startedAt ) }-${ sessionId }.jsonl`;
+		const filePath = path.join( directory, fileName );
+
+		await fs.mkdir( directory, { recursive: true } );
+
+		const recorder = new AiSessionRecorder( sessionId, filePath );
+		await recorder.appendEvent( {
+			type: 'session.started',
+			timestamp: toIsoTimestamp( startedAt ),
+			version: 1,
+			sessionId,
+		} );
+
+		return recorder;
+	}
+
+	static async open( options: {
+		sessionId: string;
+		filePath: string;
+		linkedAgentSessionIds?: string[];
+	} ): Promise< AiSessionRecorder > {
+		await fs.access( options.filePath );
+		return new AiSessionRecorder(
+			options.sessionId,
+			options.filePath,
+			options.linkedAgentSessionIds ?? []
+		);
+	}
+
+	async recordAgentSessionId( agentSessionId: string ): Promise< void > {
+		if ( this.linkedAgentSessionIds.has( agentSessionId ) ) {
+			return;
+		}
+
+		this.linkedAgentSessionIds.add( agentSessionId );
+		await this.appendEvent( {
+			type: 'session.linked',
+			timestamp: toIsoTimestamp(),
+			agentSessionId,
+		} );
+	}
+
+	async recordSiteSelected( site: { name: string; path: string } ): Promise< void > {
+		await this.appendEvent( {
+			type: 'site.selected',
+			timestamp: toIsoTimestamp(),
+			siteName: site.name,
+			sitePath: site.path,
+		} );
+	}
+
+	async recordUserMessage( options: {
+		text: string;
+		source: 'prompt' | 'ask_user';
+		sitePath?: string;
+	} ): Promise< void > {
+		await this.appendEvent( {
+			type: 'user.message',
+			timestamp: toIsoTimestamp(),
+			text: options.text,
+			source: options.source,
+			sitePath: options.sitePath,
+		} );
+	}
+
+	async recordAssistantMessage( blocks: AssistantMessageBlock[] ): Promise< void > {
+		if ( blocks.length === 0 ) {
+			return;
+		}
+
+		await this.appendEvent( {
+			type: 'assistant.message',
+			timestamp: toIsoTimestamp(),
+			blocks,
+		} );
+	}
+
+	async recordToolResult( options: { ok: boolean; text: string } ): Promise< void > {
+		await this.appendEvent( {
+			type: 'tool.result',
+			timestamp: toIsoTimestamp(),
+			ok: options.ok,
+			text: options.text,
+		} );
+	}
+
+	async recordToolProgress( message: string ): Promise< void > {
+		if ( ! message.trim() ) {
+			return;
+		}
+
+		await this.appendEvent( {
+			type: 'tool.progress',
+			timestamp: toIsoTimestamp(),
+			message,
+		} );
+	}
+
+	async recordAgentQuestion( options: {
+		question: string;
+		options: Array< {
+			label: string;
+			description: string;
+		} >;
+	} ): Promise< void > {
+		await this.appendEvent( {
+			type: 'agent.question',
+			timestamp: toIsoTimestamp(),
+			question: options.question,
+			options: options.options,
+		} );
+	}
+
+	async recordTurnClosed( status: TurnStatus ): Promise< void > {
+		await this.appendEvent( {
+			type: 'turn.closed',
+			timestamp: toIsoTimestamp(),
+			status,
+		} );
+	}
+
+	private async appendEvent( event: AiSessionEvent ): Promise< void > {
+		await fs.appendFile( this.filePath, `${ JSON.stringify( event ) }\n`, {
+			encoding: 'utf8',
+		} );
+	}
+}
diff --git a/apps/cli/ai/sessions/replay.ts b/apps/cli/ai/sessions/replay.ts
new file mode 100644
index 0000000000..d0ac59731d
--- /dev/null
+++ b/apps/cli/ai/sessions/replay.ts
@@ -0,0 +1,65 @@
+import path from 'path';
+import { AiChatUI } from 'cli/ai/ui';
+import { toReplayAssistantMessage, toReplayToolResultMessage } from './parser';
+import type { AiSessionEvent } from './types';
+
+export function replaySessionHistory( ui: AiChatUI, events: AiSessionEvent[] ): void {
+	ui.prepareForReplay();
+
+	try {
+		for ( const event of events ) {
+			if ( event.type === 'site.selected' ) {
+				ui.setActiveSite(
+					{
+						name: event.siteName,
+						path: event.sitePath,
+						running: false,
+					},
+					{ announce: false, emitEvent: false }
+				);
+				continue;
+			}
+
+			if ( event.type === 'user.message' ) {
+				if ( event.sitePath && ( ! ui.activeSite || ui.activeSite.path !== event.sitePath ) ) {
+					ui.setActiveSite(
+						{
+							name: path.basename( event.sitePath ),
+							path: event.sitePath,
+							running: false,
+						},
+						{ announce: false, emitEvent: false }
+					);
+				}
+				ui.addUserMessage( event.text );
+				continue;
+			}
+
+			if ( event.type === 'assistant.message' ) {
+				ui.handleMessage( toReplayAssistantMessage( event.blocks ) );
+				continue;
+			}
+
+			if ( event.type === 'tool.result' ) {
+				ui.handleMessage( toReplayToolResultMessage( event ) );
+				continue;
+			}
+
+			if ( event.type === 'tool.progress' ) {
+				ui.setLoaderMessage( event.message );
+				continue;
+			}
+
+			if ( event.type === 'agent.question' ) {
+				ui.showAgentQuestion( event.question, event.options );
+				continue;
+			}
+
+			if ( event.type === 'turn.closed' ) {
+				ui.endAgentTurn();
+			}
+		}
+	} finally {
+		ui.finishReplay();
+	}
+}
diff --git a/apps/cli/ai/sessions/store.ts b/apps/cli/ai/sessions/store.ts
new file mode 100644
index 0000000000..b593ca6ad9
--- /dev/null
+++ b/apps/cli/ai/sessions/store.ts
@@ -0,0 +1,140 @@
+import fs from 'fs/promises';
+import path from 'path';
+import { getAiSessionsRootDirectory } from './paths';
+import { readAiSessionSummaryFromEvents } from './summary';
+import type { AiSessionEvent, AiSessionSummary, LoadedAiSession } from './types';
+
+export async function readAiSessionEventsFromFile( filePath: string ): Promise< AiSessionEvent[] > {
+	const content = await fs.readFile( filePath, 'utf8' );
+	const lines = content
+		.split( '\n' )
+		.map( ( line ) => line.trim() )
+		.filter( ( line ) => line.length > 0 );
+	const events: AiSessionEvent[] = [];
+
+	for ( const line of lines ) {
+		try {
+			events.push( JSON.parse( line ) as AiSessionEvent );
+		} catch {
+			// Ignore malformed lines and keep loading the rest.
+		}
+	}
+
+	return events;
+}
+
+async function listSessionFilesRecursively( directory: string ): Promise< string[] > {
+	try {
+		const entries = await fs.readdir( directory, { withFileTypes: true, encoding: 'utf8' } );
+
+		const nestedFiles = await Promise.all(
+			entries.map( async ( entry ) => {
+				const fullPath = path.join( directory, entry.name );
+
+				if ( entry.isDirectory() ) {
+					return listSessionFilesRecursively( fullPath );
+				}
+
+				if ( entry.isFile() && entry.name.endsWith( '.jsonl' ) ) {
+					return [ fullPath ];
+				}
+
+				return [];
+			} )
+		);
+
+		return nestedFiles.flat();
+	} catch ( error ) {
+		const fsError = error as NodeJS.ErrnoException;
+		if ( fsError.code === 'ENOENT' ) {
+			return [];
+		}
+
+		throw error;
+	}
+}
+
+async function resolveSessionByIdOrPrefix(
+	sessionIdOrPrefix: string
+): Promise< AiSessionSummary > {
+	const sessions = await listAiSessions();
+	const exactMatch = sessions.find( ( session ) => session.id === sessionIdOrPrefix );
+	const candidates = exactMatch
+		? [ exactMatch ]
+		: sessions.filter( ( session ) => session.id.startsWith( sessionIdOrPrefix ) );
+
+	if ( candidates.length === 0 ) {
+		throw new Error( `AI session not found: ${ sessionIdOrPrefix }` );
+	}
+
+	if ( candidates.length > 1 ) {
+		const sample = candidates
+			.slice( 0, 5 )
+			.map( ( session ) => session.id )
+			.join( ', ' );
+		throw new Error(
+			`Session id prefix is ambiguous: ${ sessionIdOrPrefix }. Matches: ${ sample }${
+				candidates.length > 5 ? ', …' : ''
+			}`
+		);
+	}
+
+	return candidates[ 0 ];
+}
+
+async function pruneEmptySessionDirectories( startDirectory: string ): Promise< void > {
+	const rootDirectory = getAiSessionsRootDirectory();
+	let currentDirectory = startDirectory;
+
+	while (
+		currentDirectory.startsWith( rootDirectory + path.sep ) &&
+		currentDirectory !== rootDirectory
+	) {
+		try {
+			await fs.rmdir( currentDirectory );
+		} catch ( error ) {
+			const fsError = error as NodeJS.ErrnoException;
+			if ( fsError.code === 'ENOTEMPTY' || fsError.code === 'ENOENT' ) {
+				return;
+			}
+
+			throw error;
+		}
+
+		currentDirectory = path.dirname( currentDirectory );
+	}
+}
+
+export async function listAiSessions(): Promise< AiSessionSummary[] > {
+	const sessionFiles = await listSessionFilesRecursively( getAiSessionsRootDirectory() );
+	const results = await Promise.allSettled(
+		sessionFiles.map( async ( filePath ) => {
+			const events = await readAiSessionEventsFromFile( filePath );
+			return readAiSessionSummaryFromEvents( filePath, events );
+		} )
+	);
+
+	const sessions = results
+		.filter(
+			( result ): result is PromiseFulfilledResult< AiSessionSummary | undefined > =>
+				result.status === 'fulfilled'
+		)
+		.map( ( result ) => result.value )
+		.filter( ( session ): session is AiSessionSummary => !! session );
+
+	return sessions.sort( ( a, b ) => Date.parse( b.updatedAt ) - Date.parse( a.updatedAt ) );
+}
+
+export async function loadAiSession( sessionIdOrPrefix: string ): Promise< LoadedAiSession > {
+	const summary = await resolveSessionByIdOrPrefix( sessionIdOrPrefix );
+	const events = await readAiSessionEventsFromFile( summary.filePath );
+	return { summary, events };
+}
+
+export async function deleteAiSession( sessionIdOrPrefix: string ): Promise< AiSessionSummary > {
+	const sessionToDelete = await resolveSessionByIdOrPrefix( sessionIdOrPrefix );
+	await fs.rm( sessionToDelete.filePath, { force: false } );
+	await pruneEmptySessionDirectories( path.dirname( sessionToDelete.filePath ) );
+
+	return sessionToDelete;
+}
diff --git a/apps/cli/ai/sessions/summary.ts b/apps/cli/ai/sessions/summary.ts
new file mode 100644
index 0000000000..9a2ba8a643
--- /dev/null
+++ b/apps/cli/ai/sessions/summary.ts
@@ -0,0 +1,80 @@
+import fs from 'fs/promises';
+import path from 'path';
+import type { AiSessionEvent, AiSessionSummary } from './types';
+
+function getSessionIdFromPath( filePath: string ): string {
+	const fileName = path.basename( filePath, '.jsonl' );
+	const uuidMatch = fileName.match(
+		/\b([0-9a-f]{8}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{12})\b/i
+	);
+	return uuidMatch?.[ 1 ] ?? fileName;
+}
+
+export async function readAiSessionSummaryFromEvents(
+	filePath: string,
+	events: AiSessionEvent[]
+): Promise< AiSessionSummary | undefined > {
+	if ( events.length === 0 ) {
+		return undefined;
+	}
+
+	const linkedAgentSessionIds: string[] = [];
+	let createdAt: string | undefined;
+	let updatedAt: string | undefined;
+	let sessionId = getSessionIdFromPath( filePath );
+	let firstPrompt: string | undefined;
+	let selectedSiteName: string | undefined;
+	let endReason: 'error' | 'stopped' | undefined;
+	let eventCount = 0;
+
+	for ( const event of events ) {
+		eventCount += 1;
+		updatedAt = event.timestamp;
+
+		if ( event.type === 'session.started' ) {
+			createdAt = event.timestamp;
+			if ( event.sessionId.trim().length > 0 ) {
+				sessionId = event.sessionId;
+			}
+		}
+
+		if (
+			event.type === 'session.linked' &&
+			! linkedAgentSessionIds.includes( event.agentSessionId )
+		) {
+			linkedAgentSessionIds.push( event.agentSessionId );
+		}
+
+		if ( event.type === 'site.selected' ) {
+			selectedSiteName = event.siteName;
+		}
+
+		if ( event.type === 'user.message' && event.source === 'prompt' && ! firstPrompt ) {
+			firstPrompt = event.text;
+		}
+
+		if ( event.type === 'turn.closed' ) {
+			if ( event.status === 'error' ) {
+				endReason = 'error';
+			} else if ( event.status === 'interrupted' ) {
+				endReason = 'stopped';
+			}
+		}
+	}
+
+	const stats = await fs.stat( filePath );
+	const fallbackTimestamp = stats.mtime.toISOString();
+
+	return {
+		id: sessionId,
+		filePath,
+		createdAt: createdAt ?? fallbackTimestamp,
+		updatedAt: updatedAt ?? createdAt ?? fallbackTimestamp,
+		agentSessionId: linkedAgentSessionIds[ linkedAgentSessionIds.length - 1 ],
+		linkedAgentSessionIds,
+		firstPrompt,
+		selectedSiteName,
+		endReason,
+		eventCount,
+	};
+}
diff --git a/apps/cli/ai/sessions/types.ts b/apps/cli/ai/sessions/types.ts
new file mode 100644
index 0000000000..fccc8f6fde
--- /dev/null
+++ b/apps/cli/ai/sessions/types.ts
@@ -0,0 +1,86 @@
+export type TurnStatus = 'success' | 'error' | 'max_turns' | 'interrupted';
+
+export type AssistantMessageBlock =
+	| {
+			type: 'text';
+			text: string;
+	  }
+	| {
+			type: 'tool_use';
+			name: string;
+			detail?: string;
+	  };
+
+export type AiSessionEvent =
+	| {
+			type: 'session.started';
+			timestamp: string;
+			version: 1;
+			sessionId: string;
+	  }
+	| {
+			type: 'session.linked';
+			timestamp: string;
+			agentSessionId: string;
+	  }
+	| {
+			type: 'site.selected';
+			timestamp: string;
+			siteName: string;
+			sitePath: string;
+	  }
+	| {
+			type: 'user.message';
+			timestamp: string;
+			text: string;
+			source: 'prompt' | 'ask_user';
+			sitePath?: string;
+	  }
+	| {
+			type: 'assistant.message';
+			timestamp: string;
+			blocks: AssistantMessageBlock[];
+	  }
+	| {
+			type: 'tool.result';
+			timestamp: string;
+			ok: boolean;
+			text: string;
+	  }
+	| {
+			type: 'tool.progress';
+			timestamp: string;
+			message: string;
+	  }
+	| {
+			type: 'agent.question';
+			timestamp: string;
+			question: string;
+			options: Array< {
+				label: string;
+				description: string;
+			} >;
+	  }
+	| {
+			type: 'turn.closed';
+			timestamp: string;
+			status: TurnStatus;
+	  };
+
+export interface AiSessionSummary {
+	id: string;
+	filePath: string;
+	createdAt: string;
+	updatedAt: string;
+	agentSessionId?: string;
+	linkedAgentSessionIds: string[];
+	firstPrompt?: string;
+	selectedSiteName?: string;
+	endReason?: 'error' | 'stopped';
+	eventCount: number;
+}
+
+export interface LoadedAiSession {
+	summary: AiSessionSummary;
+	events: AiSessionEvent[];
+}
diff --git a/apps/cli/commands/ai/index.ts b/apps/cli/commands/ai/index.ts
index 8af9647ee6..be58065905 100644
--- a/apps/cli/commands/ai/index.ts
+++ b/apps/cli/commands/ai/index.ts
@@ -25,7 +25,6 @@ import { runCommand as runLogoutCommand } from 'cli/commands/auth/logout';
 import { getAnthropicApiKey, getAuthToken } from 'cli/lib/appdata';
 import { Logger, LoggerError, setProgressCallback } from 'cli/logger';
 import { StudioArgv } from 'cli/types';
-import type { SDKMessage } from '@anthropic-ai/claude-agent-sdk';
 
 const logger = new Logger< string >();
 
@@ -309,7 +308,7 @@ export async function runCommand(): Promise< void > {
 
 		try {
 			for await ( const message of agentQuery ) {
-				const assistantBlocks = extractAssistantMessageBlocks( message );
+				const assistantBlocks = extractAssistantMessageBlocks( message, getToolDetail );
 				if ( assistantBlocks.length > 0 ) {
 					await persist( ( recorder ) => recorder.recordAssistantMessage( assistantBlocks ) );
 				}
diff --git a/apps/cli/commands/ai/sessions/delete.ts b/apps/cli/commands/ai/sessions/delete.ts
index 0aff012936..8ee4b690a6 100644
--- a/apps/cli/commands/ai/sessions/delete.ts
+++ b/apps/cli/commands/ai/sessions/delete.ts
@@ -1,5 +1,5 @@
 import { __ } from '@wordpress/i18n';
-import { deleteAiSession, listAiSessions } from 'cli/ai/sessions';
+import { deleteAiSession, listAiSessions } from 'cli/ai/sessions/store';
 import { chooseSessionForAction } from 'cli/commands/ai/sessions/helpers';
 import { Logger, LoggerError } from 'cli/logger';
 import { StudioArgv } from 'cli/types';
diff --git a/apps/cli/commands/ai/sessions/helpers.ts b/apps/cli/commands/ai/sessions/helpers.ts
index 73a8281a7d..5ef90b556e 100644
--- a/apps/cli/commands/ai/sessions/helpers.ts
+++ b/apps/cli/commands/ai/sessions/helpers.ts
@@ -1,7 +1,8 @@
 import { select } from '@inquirer/prompts';
 import { __ } from '@wordpress/i18n';
 import chalk from 'chalk';
-import { listAiSessions, type AiSessionSummary } from 'cli/ai/sessions';
+import { listAiSessions } from 'cli/ai/sessions/store';
+import type { AiSessionSummary } from 'cli/ai/sessions/types';
 
 function formatSessionTimestamp( timestamp: string ): string {
 	const parsed = Date.parse( timestamp );
diff --git a/apps/cli/commands/ai/sessions/list.ts b/apps/cli/commands/ai/sessions/list.ts
index 05ad7e8c1b..5cf337419a 100644
--- a/apps/cli/commands/ai/sessions/list.ts
+++ b/apps/cli/commands/ai/sessions/list.ts
@@ -1,5 +1,5 @@
 import { __ } from '@wordpress/i18n';
-import { listAiSessions } from 'cli/ai/sessions';
+import { listAiSessions } from 'cli/ai/sessions/store';
 import { displaySessionsCompact } from 'cli/commands/ai/sessions/helpers';
 import { Logger, LoggerError } from 'cli/logger';
 import { StudioArgv } from 'cli/types';
diff --git a/apps/cli/commands/ai/sessions/resume.ts b/apps/cli/commands/ai/sessions/resume.ts
index 817b836e28..b33c215547 100644
--- a/apps/cli/commands/ai/sessions/resume.ts
+++ b/apps/cli/commands/ai/sessions/resume.ts
@@ -1,5 +1,5 @@
 import { __ } from '@wordpress/i18n';
-import { listAiSessions, loadAiSession } from 'cli/ai/sessions';
+import { listAiSessions, loadAiSession } from 'cli/ai/sessions/store';
 import { runCommand as runAiCommand } from 'cli/commands/ai';
 import { chooseSessionForAction } from 'cli/commands/ai/sessions/helpers';
 import { Logger, LoggerError } from 'cli/logger';
diff --git a/apps/cli/commands/ai/tests/ai.test.ts b/apps/cli/commands/ai/tests/ai.test.ts
index 013012b587..fa45be8680 100644
--- a/apps/cli/commands/ai/tests/ai.test.ts
+++ b/apps/cli/commands/ai/tests/ai.test.ts
@@ -1,6 +1,8 @@
+import { __ } from '@wordpress/i18n';
 import { beforeEach, describe, expect, it, vi } from 'vitest';
 import yargs from 'yargs/yargs';
-import { AiSessionRecorder, deleteAiSession, listAiSessions, loadAiSession } from 'cli/ai/sessions';
+import { AiSessionRecorder } from 'cli/ai/sessions/recorder';
+import { deleteAiSession, listAiSessions, loadAiSession } from 'cli/ai/sessions/store';
 import { registerCommand as registerAiCommand } from 'cli/commands/ai';
 import { registerCommand as registerAiSessionsDeleteCommand } from 'cli/commands/ai/sessions/delete';
 import { registerCommand as registerAiSessionsListCommand } from 'cli/commands/ai/sessions/list';
@@ -102,7 +104,7 @@ vi.mock( 'cli/ai/ui', () => ( {
 		typeof input.detail === 'string' ? input.detail : '',
 } ) );
 
-vi.mock( 'cli/ai/sessions', () => {
+vi.mock( 'cli/ai/sessions/recorder', () => {
 	class MockAiSessionRecorder {
 		static create = vi.fn().mockResolvedValue( new MockAiSessionRecorder() );
 		static open = vi.fn().mockResolvedValue( new MockAiSessionRecorder() );
@@ -118,12 +120,24 @@ vi.mock( 'cli/ai/sessions', () => {
 
 	return {
 		AiSessionRecorder: MockAiSessionRecorder,
-		listAiSessions: vi.fn(),
-		loadAiSession: vi.fn(),
-		deleteAiSession: vi.fn(),
 	};
 } );
 
+vi.mock( 'cli/ai/sessions/store', () => ( {
+	listAiSessions: vi.fn(),
+	loadAiSession: vi.fn(),
+	deleteAiSession: vi.fn(),
+} ) );
+
+vi.mock( 'cli/ai/sessions/parser', () => ( {
+	extractAssistantMessageBlocks: vi.fn().mockReturnValue( [] ),
+	extractToolResult: vi.fn().mockReturnValue( undefined ),
+} ) );
+
+vi.mock( 'cli/ai/sessions/replay', () => ( {
+	replaySessionHistory: vi.fn(),
+} ) );
+
 describe( 'CLI: studio ai sessions command', () => {
 	beforeEach( () => {
 		vi.clearAllMocks();
@@ -133,9 +147,9 @@ describe( 'CLI: studio ai sessions command', () => {
 
 	function buildParser(): StudioArgv {
 		const parser = yargs( [] ).scriptName( 'studio' ).strict().exitProcess( false ) as StudioArgv;
-		parser.command( 'ai', 'AI-powered WordPress assistant', ( aiYargs ) => {
+		parser.command( 'ai', __( 'AI-powered WordPress assistant' ), ( aiYargs ) => {
 			registerAiCommand( aiYargs as StudioArgv );
-			aiYargs.command( 'sessions', 'Manage AI sessions', ( sessionsYargs ) => {
+			aiYargs.command( 'sessions', __( 'Manage AI sessions' ), ( sessionsYargs ) => {
 				sessionsYargs
 					.option( 'path', {
 						hidden: true,
@@ -143,14 +157,14 @@ describe( 'CLI: studio ai sessions command', () => {
 					.option( 'session-persistence', {
 						type: 'boolean',
 						default: true,
-						description: 'Record this AI chat session to disk',
+						description: __( 'Record this AI chat session to disk' ),
 					} );
 				registerAiSessionsListCommand( sessionsYargs as StudioArgv );
 				registerAiSessionsResumeCommand( sessionsYargs as StudioArgv );
 				registerAiSessionsDeleteCommand( sessionsYargs as StudioArgv );
 				sessionsYargs
 					.version( false )
-					.demandCommand( 1, 'You must provide a valid ai sessions command' );
+					.demandCommand( 1, __( 'You must provide a valid ai sessions command' ) );
 			} );
 			aiYargs.version( false );
 		} );
diff --git a/apps/cli/commands/ai/tests/sessions.test.ts b/apps/cli/commands/ai/tests/sessions.test.ts
index 6468e5d20f..677cb8d9ce 100644
--- a/apps/cli/commands/ai/tests/sessions.test.ts
+++ b/apps/cli/commands/ai/tests/sessions.test.ts
@@ -2,15 +2,14 @@ import fs from 'fs/promises';
 import os from 'os';
 import path from 'path';
 import { afterEach, describe, expect, it } from 'vitest';
+import { getAiSessionsDirectoryForDate, getAiSessionsRootDirectory } from 'cli/ai/sessions/paths';
+import { AiSessionRecorder } from 'cli/ai/sessions/recorder';
 import {
-	AiSessionRecorder,
 	deleteAiSession,
-	getAiSessionsDirectoryForDate,
-	getAiSessionsRootDirectory,
-	loadAiSession,
 	listAiSessions,
+	loadAiSession,
 	readAiSessionEventsFromFile,
-} from 'cli/ai/sessions';
+} from 'cli/ai/sessions/store';
 
 describe( 'ai-sessions', () => {
 	let testRoot: string | undefined;

From 1573e19e4d0798fa72e257ecebfc8298e3a26516 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Thu, 12 Mar 2026 22:48:14 +0100
Subject: [PATCH 18/33] Restore sessions feature after rebase

---
 apps/cli/ai/ui.ts                     |  33 ++++-
 apps/cli/commands/ai/index.ts         | 176 ++++++++++----------------
 apps/cli/commands/ai/tests/ai.test.ts |   4 +
 3 files changed, 101 insertions(+), 112 deletions(-)

diff --git a/apps/cli/ai/ui.ts b/apps/cli/ai/ui.ts
index 6c1830a3dd..77fcf52722 100644
--- a/apps/cli/ai/ui.ts
+++ b/apps/cli/ai/ui.ts
@@ -451,6 +451,8 @@ export class AiChatUI {
 	private activeExpandablePreview: ExpandablePreview | null = null;
 	private _inAgentTurn = false;
 	private _activeSiteData: SiteData | null = null;
+	private siteSelectedCallback: ( ( site: SiteInfo ) => void ) | null = null;
+	private replayMode = false;
 	private pendingToolCalls = new Map<
 		string,
 		{ name: string; input: Record< string, unknown > }
@@ -548,6 +550,27 @@ export class AiChatUI {
 		this.siteSelectedCallback = fn;
 	}
 
+	prepareForReplay(): void {
+		this.replayMode = true;
+		this.hideLoader();
+		this.currentMarkdown = null;
+		this.currentResponseText = '';
+	}
+
+	finishReplay(): void {
+		this.replayMode = false;
+		this.hideLoader();
+		this.currentMarkdown = null;
+		this.currentResponseText = '';
+	}
+
+	showAgentQuestion(
+		question: string,
+		options: Array< { label: string; description: string } >
+	): void {
+		this.showInfo( `${ question } — ${ options.map( ( option ) => option.label ).join( ' / ' ) }` );
+	}
+
 	constructor() {
 		const terminal = new ProcessTerminal();
 		this.tui = new TUI( terminal );
@@ -898,12 +921,18 @@ export class AiChatUI {
 		this.tui.requestRender();
 	}
 
-	private setActiveSite( site: SiteInfo ): void {
+	setActiveSite( site: SiteInfo, options: { announce?: boolean; emitEvent?: boolean } = {} ): void {
+		const { announce = true, emitEvent = true } = options;
 		this._activeSite = site;
 		this.editor.activeSiteName = site.name;
 		const suffix = site.remote ? ' (WordPress.com)' : '';
 		const label = ` ✻ Selected site: ${ site.name }${ suffix }`;
-		this.messages.addChild( new Text( `${ chalk.hex( '#5b8db8' )( label ) }\n`, 0, 0 ) );
+		if ( announce ) {
+			this.messages.addChild( new Text( `${ chalk.hex( '#5b8db8' )( label ) }\n`, 0, 0 ) );
+		}
+		if ( emitEvent ) {
+			this.siteSelectedCallback?.( site );
+		}
 		this.tui.requestRender();
 	}
 
diff --git a/apps/cli/commands/ai/index.ts b/apps/cli/commands/ai/index.ts
index be58065905..f1e89cfaf2 100644
--- a/apps/cli/commands/ai/index.ts
+++ b/apps/cli/commands/ai/index.ts
@@ -1,5 +1,11 @@
 import { __ } from '@wordpress/i18n';
-import { AI_MODELS, DEFAULT_MODEL, startAiAgent, type AiModelId } from 'cli/ai/agent';
+import {
+	AI_MODELS,
+	DEFAULT_MODEL,
+	startAiAgent,
+	type AiModelId,
+	type AskUserQuestion,
+} from 'cli/ai/agent';
 import {
 	getAvailableAiProviders,
 	isAiProviderReady,
@@ -10,6 +16,10 @@ import {
 	saveSelectedAiProvider,
 } from 'cli/ai/auth';
 import { AI_PROVIDERS, type AiProviderId } from 'cli/ai/providers';
+import { extractAssistantMessageBlocks, extractToolResult } from 'cli/ai/sessions/parser';
+import { AiSessionRecorder } from 'cli/ai/sessions/recorder';
+import { replaySessionHistory } from 'cli/ai/sessions/replay';
+import { type LoadedAiSession, type TurnStatus } from 'cli/ai/sessions/types';
 import {
 	AI_CHAT_API_KEY_COMMAND,
 	AI_CHAT_BROWSER_COMMAND,
@@ -19,7 +29,7 @@ import {
 	AI_CHAT_MODEL_COMMAND,
 	AI_CHAT_PROVIDER_COMMAND,
 } from 'cli/ai/slash-commands';
-import { AiChatUI } from 'cli/ai/ui';
+import { AiChatUI, getToolDetail } from 'cli/ai/ui';
 import { runCommand as runLoginCommand } from 'cli/commands/auth/login';
 import { runCommand as runLogoutCommand } from 'cli/commands/auth/logout';
 import { getAnthropicApiKey, getAuthToken } from 'cli/lib/appdata';
@@ -43,117 +53,12 @@ function getErrorMessage( error: unknown ): string {
 	return String( error );
 }
 
-function extractAssistantMessageBlocks( message: SDKMessage ): AssistantMessageBlock[] {
-	if ( message.type !== 'assistant' ) {
-		return [];
-	}
-
-	const blocks: AssistantMessageBlock[] = [];
-	for ( const block of message.message.content ) {
-		if ( block.type === 'text' && block.text ) {
-			blocks.push( {
-				type: 'text',
-				text: block.text,
-			} );
-		}
-
-		if ( block.type === 'tool_use' && block.name ) {
-			const detail =
-				block.input && typeof block.input === 'object'
-					? getToolDetail( block.name, block.input as Record< string, unknown > )
-					: '';
-			blocks.push( {
-				type: 'tool_use',
-				name: block.name,
-				detail: detail || undefined,
-			} );
-		}
-	}
-
-	return blocks;
-}
-
-function toToolResultText( value: unknown ): string {
-	if ( Array.isArray( value ) ) {
-		const lines = value
-			.map( ( item ) => {
-				if ( typeof item === 'string' ) {
-					return item;
-				}
-
-				if ( item && typeof item === 'object' ) {
-					const typedItem = item as { type?: unknown; text?: unknown };
-					if ( typedItem.type === 'text' && typeof typedItem.text === 'string' ) {
-						return typedItem.text;
-					}
-
-					try {
-						return JSON.stringify( item, null, 2 );
-					} catch {
-						return String( item );
-					}
-				}
-
-				return String( item );
-			} )
-			.map( ( line ) => line.trim() )
-			.filter( ( line ) => line.length > 0 );
-
-		return lines.join( '\n' );
-	}
-
-	if ( typeof value === 'string' ) {
-		return value.trim();
-	}
-
-	if ( value === null || value === undefined ) {
-		return '';
-	}
-
-	try {
-		return JSON.stringify( value, null, 2 );
-	} catch {
-		return String( value );
-	}
-}
-
-function extractToolResult( message: SDKMessage ): { ok: boolean; text: string } | undefined {
-	if ( message.type !== 'user' ) {
-		return undefined;
-	}
-
-	const rawResult = message.tool_use_result;
-	if ( ! rawResult ) {
-		return undefined;
-	}
-
-	if ( typeof rawResult !== 'object' ) {
-		const text = String( rawResult ).trim();
-		return {
-			ok: true,
-			text,
-		};
-	}
-
-	const typedResult = rawResult as {
-		content?: unknown;
-		isError?: unknown;
-		is_error?: unknown;
-	};
-	const isError = typedResult.isError === true || typedResult.is_error === true;
-	const textFromContent = toToolResultText( typedResult.content );
-
-	return {
-		ok: ! isError,
-		text: textFromContent,
-	};
-}
-
-export async function runCommand(): Promise< void > {
+export async function runCommand(
+	options: { resumeSession?: LoadedAiSession; noSessionPersistence?: boolean } = {}
+): Promise< void > {
 	const ui = new AiChatUI();
 	let currentProvider: AiProviderId = await resolveInitialAiProvider();
 	ui.currentProvider = currentProvider;
-	setProgressCallback( ( message ) => ui.setLoaderMessage( message ) );
 	ui.start();
 	ui.showWelcome();
 
@@ -203,6 +108,23 @@ export async function runCommand(): Promise< void > {
 
 	let currentModel: AiModelId = DEFAULT_MODEL;
 
+	ui.onSiteSelected = ( site ) => {
+		void persist( ( recorder ) =>
+			recorder.recordSiteSelected( {
+				name: site.name,
+				path: site.path,
+			} )
+		);
+	};
+
+	if ( options.resumeSession ) {
+		ui.showInfo( `Resuming session ${ options.resumeSession.summary.id }` );
+		replaySessionHistory( ui, options.resumeSession.events );
+		if ( ! sessionId ) {
+			ui.showInfo( 'No linked Claude session was found. Continuing from transcript only.' );
+		}
+	}
+
 	async function prepareProviderSelection(
 		provider: AiProviderId,
 		options?: { force?: boolean }
@@ -267,6 +189,40 @@ export async function runCommand(): Promise< void > {
 		ui.showInfo( 'No Anthropic API key saved. Use /provider to enter one.' );
 	}
 
+	async function askUserAndPersistAnswers(
+		questions: AskUserQuestion[]
+	): Promise< Record< string, string > > {
+		for ( const question of questions ) {
+			await persist( ( recorder ) =>
+				recorder.recordAgentQuestion( {
+					question: question.question,
+					options: question.options.map( ( option ) => ( {
+						label: option.label,
+						description: option.description,
+					} ) ),
+				} )
+			);
+		}
+
+		const answers = await ui.askUser( questions );
+		for ( const question of questions ) {
+			const answer = answers[ question.question ];
+			if ( typeof answer !== 'string' || ! answer.trim() ) {
+				continue;
+			}
+
+			await persist( ( recorder ) =>
+				recorder.recordUserMessage( {
+					text: answer,
+					source: 'ask_user',
+					sitePath: ui.activeSite?.path,
+				} )
+			);
+		}
+
+		return answers;
+	}
+
 	async function runAgentTurn( prompt: string ): Promise< void > {
 		const env = await resolveAiEnvironment( currentProvider );
 		ui.beginAgentTurn();
diff --git a/apps/cli/commands/ai/tests/ai.test.ts b/apps/cli/commands/ai/tests/ai.test.ts
index fa45be8680..2fa8444bb4 100644
--- a/apps/cli/commands/ai/tests/ai.test.ts
+++ b/apps/cli/commands/ai/tests/ai.test.ts
@@ -19,6 +19,10 @@ vi.mock( 'cli/lib/appdata', () => ( {
 	saveAnthropicApiKey: vi.fn(),
 } ) );
 
+vi.mock( 'cli/ai/auth', () => ( {
+	resolveInitialAiProvider: vi.fn().mockResolvedValue( 'anthropic-api-key' ),
+} ) );
+
 vi.mock( 'cli/logger', () => ( {
 	Logger: class {
 		reportStart = vi.fn();

From 971e61183cb821212f015a1f1b921fed6a4a4dbd Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Fri, 13 Mar 2026 00:00:39 +0100
Subject: [PATCH 19/33] Stop differentiating assistant.message and tool.result

---
 apps/cli/ai/sessions/parser.ts              | 166 --------------------
 apps/cli/ai/sessions/recorder.ts            |  28 +---
 apps/cli/ai/sessions/replay.ts              |  17 +-
 apps/cli/ai/sessions/types.ts               |  23 +--
 apps/cli/ai/ui.ts                           |  65 +++++---
 apps/cli/commands/ai/index.ts               |  48 +++---
 apps/cli/commands/ai/tests/ai.test.ts       |   8 +-
 apps/cli/commands/ai/tests/sessions.test.ts | 118 ++++++++++++--
 8 files changed, 193 insertions(+), 280 deletions(-)
 delete mode 100644 apps/cli/ai/sessions/parser.ts

diff --git a/apps/cli/ai/sessions/parser.ts b/apps/cli/ai/sessions/parser.ts
deleted file mode 100644
index e7d23f1493..0000000000
--- a/apps/cli/ai/sessions/parser.ts
+++ /dev/null
@@ -1,166 +0,0 @@
-import type { AssistantMessageBlock } from './types';
-import type { SDKMessage } from '@anthropic-ai/claude-agent-sdk';
-
-type ToolDetailResolver = ( name: string, input: Record< string, unknown > ) => string;
-
-export function extractAssistantMessageBlocks(
-	message: SDKMessage,
-	resolveToolDetail: ToolDetailResolver
-): AssistantMessageBlock[] {
-	if ( message.type !== 'assistant' ) {
-		return [];
-	}
-
-	const blocks: AssistantMessageBlock[] = [];
-	for ( const block of message.message.content ) {
-		if ( block.type === 'text' && block.text ) {
-			blocks.push( {
-				type: 'text',
-				text: block.text,
-			} );
-		}
-
-		if ( block.type === 'tool_use' && block.name ) {
-			const detail =
-				block.input && typeof block.input === 'object'
-					? resolveToolDetail( block.name, block.input as Record< string, unknown > )
-					: '';
-			blocks.push( {
-				type: 'tool_use',
-				name: block.name,
-				detail: detail || undefined,
-			} );
-		}
-	}
-
-	return blocks;
-}
-
-function toToolResultText( value: unknown ): string {
-	if ( Array.isArray( value ) ) {
-		const lines = value
-			.map( ( item ) => {
-				if ( typeof item === 'string' ) {
-					return item;
-				}
-
-				if ( item && typeof item === 'object' ) {
-					const typedItem = item as { type?: unknown; text?: unknown };
-					if ( typedItem.type === 'text' && typeof typedItem.text === 'string' ) {
-						return typedItem.text;
-					}
-
-					try {
-						return JSON.stringify( item, null, 2 );
-					} catch {
-						return String( item );
-					}
-				}
-
-				return String( item );
-			} )
-			.map( ( line ) => line.trim() )
-			.filter( ( line ) => line.length > 0 );
-
-		return lines.join( '\n' );
-	}
-
-	if ( typeof value === 'string' ) {
-		return value.trim();
-	}
-
-	if ( value === null || value === undefined ) {
-		return '';
-	}
-
-	try {
-		return JSON.stringify( value, null, 2 );
-	} catch {
-		return String( value );
-	}
-}
-
-export function extractToolResult(
-	message: SDKMessage
-): { ok: boolean; text: string } | undefined {
-	if ( message.type !== 'user' ) {
-		return undefined;
-	}
-
-	const rawResult = message.tool_use_result;
-	if ( ! rawResult ) {
-		return undefined;
-	}
-
-	if ( typeof rawResult !== 'object' ) {
-		const text = String( rawResult ).trim();
-		return {
-			ok: true,
-			text,
-		};
-	}
-
-	const typedResult = rawResult as {
-		content?: unknown;
-		isError?: unknown;
-		is_error?: unknown;
-	};
-	const isError = typedResult.isError === true || typedResult.is_error === true;
-	const textFromContent = toToolResultText( typedResult.content );
-
-	return {
-		ok: ! isError,
-		text: textFromContent,
-	};
-}
-
-function toReplayToolInput( _name: string, detail?: string ): Record< string, unknown > {
-	if ( ! detail ) {
-		return {};
-	}
-
-	return { detail };
-}
-
-export function toReplayAssistantMessage( blocks: AssistantMessageBlock[] ): SDKMessage {
-	return {
-		type: 'assistant',
-		message: {
-			content: blocks.map( ( block, index ) => {
-				if ( block.type === 'text' ) {
-					return {
-						type: 'text',
-						text: block.text,
-					};
-				}
-
-				return {
-					type: 'tool_use',
-					id: `replay-tool-${ index }`,
-					name: block.name,
-					input: toReplayToolInput( block.name, block.detail ),
-				};
-			} ),
-		},
-	} as SDKMessage;
-}
-
-export function toReplayToolResultMessage( options: { ok: boolean; text: string } ): SDKMessage {
-	const normalizedText = options.text.trim();
-	const content = ! normalizedText
-		? []
-		: [
-				{
-					type: 'text',
-					text: options.text,
-				},
-		  ];
-
-	return {
-		type: 'user',
-		tool_use_result: {
-			isError: ! options.ok,
-			content,
-		},
-	} as SDKMessage;
-}
diff --git a/apps/cli/ai/sessions/recorder.ts b/apps/cli/ai/sessions/recorder.ts
index 14fdcfde48..2edbcf8789 100644
--- a/apps/cli/ai/sessions/recorder.ts
+++ b/apps/cli/ai/sessions/recorder.ts
@@ -2,7 +2,8 @@ import crypto from 'crypto';
 import fs from 'fs/promises';
 import path from 'path';
 import { getAiSessionsDirectoryForDate } from './paths';
-import type { AiSessionEvent, AssistantMessageBlock, TurnStatus } from './types';
+import type { AiSessionEvent, TurnStatus } from './types';
+import type { SDKMessage } from '@anthropic-ai/claude-agent-sdk';
 
 function toSortableTimestampPrefix( date: Date ): string {
 	return date
@@ -96,35 +97,22 @@ export class AiSessionRecorder {
 		} );
 	}
 
-	async recordAssistantMessage( blocks: AssistantMessageBlock[] ): Promise< void > {
-		if ( blocks.length === 0 ) {
-			return;
-		}
-
-		await this.appendEvent( {
-			type: 'assistant.message',
-			timestamp: toIsoTimestamp(),
-			blocks,
-		} );
-	}
-
-	async recordToolResult( options: { ok: boolean; text: string } ): Promise< void > {
+	async recordSdkMessage( message: SDKMessage, timestamp?: string ): Promise< void > {
 		await this.appendEvent( {
-			type: 'tool.result',
-			timestamp: toIsoTimestamp(),
-			ok: options.ok,
-			text: options.text,
+			type: 'sdk.message',
+			timestamp: timestamp ?? toIsoTimestamp(),
+			message,
 		} );
 	}
 
-	async recordToolProgress( message: string ): Promise< void > {
+	async recordToolProgress( message: string, timestamp?: string ): Promise< void > {
 		if ( ! message.trim() ) {
 			return;
 		}
 
 		await this.appendEvent( {
 			type: 'tool.progress',
-			timestamp: toIsoTimestamp(),
+			timestamp: timestamp ?? toIsoTimestamp(),
 			message,
 		} );
 	}
diff --git a/apps/cli/ai/sessions/replay.ts b/apps/cli/ai/sessions/replay.ts
index d0ac59731d..d3b567153e 100644
--- a/apps/cli/ai/sessions/replay.ts
+++ b/apps/cli/ai/sessions/replay.ts
@@ -1,6 +1,5 @@
 import path from 'path';
 import { AiChatUI } from 'cli/ai/ui';
-import { toReplayAssistantMessage, toReplayToolResultMessage } from './parser';
 import type { AiSessionEvent } from './types';
 
 export function replaySessionHistory( ui: AiChatUI, events: AiSessionEvent[] ): void {
@@ -8,6 +7,8 @@ export function replaySessionHistory( ui: AiChatUI, events: AiSessionEvent[] ):
 
 	try {
 		for ( const event of events ) {
+			ui.setReplayTimestamp( event.timestamp );
+
 			if ( event.type === 'site.selected' ) {
 				ui.setActiveSite(
 					{
@@ -21,6 +22,10 @@ export function replaySessionHistory( ui: AiChatUI, events: AiSessionEvent[] ):
 			}
 
 			if ( event.type === 'user.message' ) {
+				if ( event.source === 'ask_user' ) {
+					continue;
+				}
+
 				if ( event.sitePath && ( ! ui.activeSite || ui.activeSite.path !== event.sitePath ) ) {
 					ui.setActiveSite(
 						{
@@ -31,17 +36,13 @@ export function replaySessionHistory( ui: AiChatUI, events: AiSessionEvent[] ):
 						{ announce: false, emitEvent: false }
 					);
 				}
+				ui.beginAgentTurn();
 				ui.addUserMessage( event.text );
 				continue;
 			}
 
-			if ( event.type === 'assistant.message' ) {
-				ui.handleMessage( toReplayAssistantMessage( event.blocks ) );
-				continue;
-			}
-
-			if ( event.type === 'tool.result' ) {
-				ui.handleMessage( toReplayToolResultMessage( event ) );
+			if ( event.type === 'sdk.message' ) {
+				ui.handleMessage( event.message );
 				continue;
 			}
 
diff --git a/apps/cli/ai/sessions/types.ts b/apps/cli/ai/sessions/types.ts
index fccc8f6fde..136ea18bb8 100644
--- a/apps/cli/ai/sessions/types.ts
+++ b/apps/cli/ai/sessions/types.ts
@@ -1,15 +1,6 @@
-export type TurnStatus = 'success' | 'error' | 'max_turns' | 'interrupted';
+import type { SDKMessage } from '@anthropic-ai/claude-agent-sdk';
 
-export type AssistantMessageBlock =
-	| {
-			type: 'text';
-			text: string;
-	  }
-	| {
-			type: 'tool_use';
-			name: string;
-			detail?: string;
-	  };
+export type TurnStatus = 'success' | 'error' | 'max_turns' | 'interrupted';
 
 export type AiSessionEvent =
 	| {
@@ -37,15 +28,9 @@ export type AiSessionEvent =
 			sitePath?: string;
 	  }
 	| {
-			type: 'assistant.message';
+			type: 'sdk.message';
 			timestamp: string;
-			blocks: AssistantMessageBlock[];
-	  }
-	| {
-			type: 'tool.result';
-			timestamp: string;
-			ok: boolean;
-			text: string;
+			message: SDKMessage;
 	  }
 	| {
 			type: 'tool.progress';
diff --git a/apps/cli/ai/ui.ts b/apps/cli/ai/ui.ts
index 77fcf52722..cf515a138d 100644
--- a/apps/cli/ai/ui.ts
+++ b/apps/cli/ai/ui.ts
@@ -246,12 +246,10 @@ const toolDisplayNames: Record< string, string > = {
 	TodoWrite: 'Update todo list',
 };
 
-export function getToolDetail( name: string, input: Record< string, unknown > ): string {
-	const fallbackDetail = typeof input.detail === 'string' ? input.detail : '';
-
+function getToolDetail( name: string, input: Record< string, unknown > ): string {
 	switch ( name ) {
 		case 'mcp__studio__site_create':
-			return typeof input.name === 'string' ? input.name : fallbackDetail;
+			return typeof input.name === 'string' ? input.name : '';
 		case 'mcp__studio__site_info':
 		case 'mcp__studio__site_start':
 		case 'mcp__studio__site_stop':
@@ -263,14 +261,14 @@ export function getToolDetail( name: string, input: Record< string, unknown > ):
 		case 'mcp__studio__preview_delete':
 			return typeof input.host === 'string' ? input.host : '';
 		case 'mcp__studio__wp_cli':
-			return typeof input.command === 'string' ? `wp ${ input.command }` : fallbackDetail;
+			return typeof input.command === 'string' ? `wp ${ input.command }` : '';
 		case 'mcp__studio__validate_blocks':
 			if ( typeof input.filePath === 'string' ) {
 				return input.filePath.split( '/' ).slice( -2 ).join( '/' );
 			}
-			return fallbackDetail || 'inline content';
+			return 'inline content';
 		case 'mcp__studio__take_screenshot':
-			return typeof input.url === 'string' ? input.url : fallbackDetail;
+			return typeof input.url === 'string' ? input.url : '';
 		case 'Read':
 		case 'Write':
 		case 'Edit': {
@@ -279,21 +277,21 @@ export function getToolDetail( name: string, input: Record< string, unknown > ):
 				const parts = filePath.split( '/' );
 				return parts.slice( -2 ).join( '/' );
 			}
-			return fallbackDetail;
+			return '';
 		}
 		case 'Bash':
 			return typeof input.command === 'string'
 				? input.command.length > 60
 					? input.command.slice( 0, 57 ) + '…'
 					: input.command
-				: fallbackDetail;
+				: '';
 		case 'Skill':
-			return typeof input.skill === 'string' ? input.skill : fallbackDetail;
+			return typeof input.skill === 'string' ? input.skill : '';
 		case 'Grep':
 		case 'Glob':
-			return typeof input.pattern === 'string' ? input.pattern : fallbackDetail;
+			return typeof input.pattern === 'string' ? input.pattern : '';
 		default:
-			return fallbackDetail;
+			return '';
 	}
 }
 
@@ -453,6 +451,7 @@ export class AiChatUI {
 	private _activeSiteData: SiteData | null = null;
 	private siteSelectedCallback: ( ( site: SiteInfo ) => void ) | null = null;
 	private replayMode = false;
+	private replayTimestampMs: number | null = null;
 	private pendingToolCalls = new Map<
 		string,
 		{ name: string; input: Record< string, unknown > }
@@ -550,8 +549,27 @@ export class AiChatUI {
 		this.siteSelectedCallback = fn;
 	}
 
+	private nowMs(): number {
+		return this.replayTimestampMs ?? Date.now();
+	}
+
+	setReplayTimestamp( timestamp?: string ): void {
+		if ( ! this.replayMode ) {
+			return;
+		}
+
+		if ( ! timestamp ) {
+			this.replayTimestampMs = null;
+			return;
+		}
+
+		const parsedTimestamp = Date.parse( timestamp );
+		this.replayTimestampMs = Number.isNaN( parsedTimestamp ) ? null : parsedTimestamp;
+	}
+
 	prepareForReplay(): void {
 		this.replayMode = true;
+		this.replayTimestampMs = null;
 		this.hideLoader();
 		this.currentMarkdown = null;
 		this.currentResponseText = '';
@@ -559,6 +577,7 @@ export class AiChatUI {
 
 	finishReplay(): void {
 		this.replayMode = false;
+		this.replayTimestampMs = null;
 		this.hideLoader();
 		this.currentMarkdown = null;
 		this.currentResponseText = '';
@@ -566,9 +585,13 @@ export class AiChatUI {
 
 	showAgentQuestion(
 		question: string,
-		options: Array< { label: string; description: string } >
+		_options: Array< { label: string; description: string } >
 	): void {
-		this.showInfo( `${ question } — ${ options.map( ( option ) => option.label ).join( ' / ' ) }` );
+		this.hideLoader();
+		this.currentMarkdown = null;
+		this.currentResponseText = '';
+		this.messages.addChild( new Text( '\n' + chalk.bold( question ), 0, 0 ) );
+		this.tui.requestRender();
 	}
 
 	constructor() {
@@ -1338,7 +1361,7 @@ export class AiChatUI {
 		this.currentResponseText = '';
 		this.hasShownResponseMarker = false;
 		this.wasInterrupted = false;
-		this.turnStartTime = Date.now();
+		this.turnStartTime = this.nowMs();
 		this.todoSnapshot = [];
 		this.latestTodoSnapshot = [];
 		this.lastRenderedTodoSignature = null;
@@ -1538,9 +1561,11 @@ export class AiChatUI {
 	}
 
 	private finalizeToolUseLine( isError: boolean, label: string ): void {
-		const elapsed = this.toolStartTime ? Date.now() - this.toolStartTime : 0;
+		const elapsed = this.toolStartTime ? this.nowMs() - this.toolStartTime : 0;
 		this.toolStartTime = null;
-		const elapsedStr = elapsed > 0 ? chalk.dim( ` (${ ( elapsed / 1000 ).toFixed( 1 ) }s)` ) : '';
+		const elapsedSeconds = Math.max( elapsed, 0 ) / 1000;
+		const elapsedStr =
+			elapsed > 0 || this.replayMode ? chalk.dim( ` (${ elapsedSeconds.toFixed( 1 ) }s)` ) : '';
 		const statusIcon = isError ? chalk.red( '⏺' ) : '⏺';
 
 		if ( this.toolDotText ) {
@@ -1789,7 +1814,7 @@ export class AiChatUI {
 						);
 						this.tui.requestRender();
 					} else if ( block.type === 'tool_use' ) {
-						this.toolStartTime = Date.now();
+						this.toolStartTime = this.nowMs();
 						const typedBlock = block as {
 							id: string;
 							name: string;
@@ -1854,7 +1879,7 @@ export class AiChatUI {
 			case 'result': {
 				this.hideLoader();
 				if ( message.subtype === 'success' ) {
-					const thinkingSec = Math.round( ( Date.now() - this.turnStartTime ) / 1000 );
+					const thinkingSec = Math.round( ( this.nowMs() - this.turnStartTime ) / 1000 );
 					if ( ! this.hasShownResponseMarker ) {
 						this.messages.addChild( new Text( '\n ' + chalk.blue( '⏺' ) + ' Done', 0, 0 ) );
 					}
@@ -1868,7 +1893,7 @@ export class AiChatUI {
 
 				// User-initiated interruption: show friendly message instead of error
 				if ( this.wasInterrupted ) {
-					const thinkingSec = Math.round( ( Date.now() - this.turnStartTime ) / 1000 );
+					const thinkingSec = Math.round( ( this.nowMs() - this.turnStartTime ) / 1000 );
 					this.messages.addChild(
 						new Text( '\n ' + chalk.yellow( '⏺' ) + ' ' + chalk.yellow( 'Interrupted' ), 0, 0 )
 					);
diff --git a/apps/cli/commands/ai/index.ts b/apps/cli/commands/ai/index.ts
index f1e89cfaf2..64a9ffedbd 100644
--- a/apps/cli/commands/ai/index.ts
+++ b/apps/cli/commands/ai/index.ts
@@ -16,7 +16,6 @@ import {
 	saveSelectedAiProvider,
 } from 'cli/ai/auth';
 import { AI_PROVIDERS, type AiProviderId } from 'cli/ai/providers';
-import { extractAssistantMessageBlocks, extractToolResult } from 'cli/ai/sessions/parser';
 import { AiSessionRecorder } from 'cli/ai/sessions/recorder';
 import { replaySessionHistory } from 'cli/ai/sessions/replay';
 import { type LoadedAiSession, type TurnStatus } from 'cli/ai/sessions/types';
@@ -29,7 +28,7 @@ import {
 	AI_CHAT_MODEL_COMMAND,
 	AI_CHAT_PROVIDER_COMMAND,
 } from 'cli/ai/slash-commands';
-import { AiChatUI, getToolDetail } from 'cli/ai/ui';
+import { AiChatUI } from 'cli/ai/ui';
 import { runCommand as runLoginCommand } from 'cli/commands/auth/login';
 import { runCommand as runLogoutCommand } from 'cli/commands/auth/logout';
 import { getAnthropicApiKey, getAuthToken } from 'cli/lib/appdata';
@@ -65,6 +64,7 @@ export async function runCommand(
 	let sessionRecorder: AiSessionRecorder | undefined;
 	let didDisableSessionPersistence = options.noSessionPersistence === true;
 	let sessionId: string | undefined = options.resumeSession?.summary.agentSessionId;
+	let persistQueue: Promise< void > = Promise.resolve();
 
 	if ( options.noSessionPersistence ) {
 		ui.showInfo( 'Session persistence disabled (--no-session-persistence).' );
@@ -85,25 +85,30 @@ export async function runCommand(
 		}
 	}
 
-	const persist = async ( callback: ( recorder: AiSessionRecorder ) => Promise< void > ) => {
-		if ( ! sessionRecorder ) {
-			return;
-		}
+	const persist = ( callback: ( recorder: AiSessionRecorder ) => Promise< void > ) => {
+		persistQueue = persistQueue.then( async () => {
+			if ( ! sessionRecorder ) {
+				return;
+			}
 
-		try {
-			await callback( sessionRecorder );
-		} catch ( error ) {
-			sessionRecorder = undefined;
-			if ( ! didDisableSessionPersistence ) {
-				didDisableSessionPersistence = true;
-				ui.showError( `Session persistence disabled: ${ getErrorMessage( error ) }` );
+			try {
+				await callback( sessionRecorder );
+			} catch ( error ) {
+				sessionRecorder = undefined;
+				if ( ! didDisableSessionPersistence ) {
+					didDisableSessionPersistence = true;
+					ui.showError( `Session persistence disabled: ${ getErrorMessage( error ) }` );
+				}
 			}
-		}
+		} );
+
+		return persistQueue;
 	};
 
 	setProgressCallback( ( message ) => {
+		const timestamp = new Date().toISOString();
 		ui.setLoaderMessage( message );
-		void persist( ( recorder ) => recorder.recordToolProgress( message ) );
+		void persist( ( recorder ) => recorder.recordToolProgress( message, timestamp ) );
 	} );
 
 	let currentModel: AiModelId = DEFAULT_MODEL;
@@ -264,17 +269,9 @@ export async function runCommand(
 
 		try {
 			for await ( const message of agentQuery ) {
-				const assistantBlocks = extractAssistantMessageBlocks( message, getToolDetail );
-				if ( assistantBlocks.length > 0 ) {
-					await persist( ( recorder ) => recorder.recordAssistantMessage( assistantBlocks ) );
-				}
-
-				const toolResult = extractToolResult( message );
-				if ( toolResult ) {
-					await persist( ( recorder ) => recorder.recordToolResult( toolResult ) );
-				}
-
+				const timestamp = new Date().toISOString();
 				const result = ui.handleMessage( message );
+				await persist( ( recorder ) => recorder.recordSdkMessage( message, timestamp ) );
 				if ( result ) {
 					sessionId = result.sessionId;
 					await persist( ( recorder ) => recorder.recordAgentSessionId( result.sessionId ) );
@@ -441,6 +438,7 @@ export async function runCommand(
 			}
 		}
 	} finally {
+		await persistQueue;
 		ui.stop();
 		process.exit( 0 );
 	}
diff --git a/apps/cli/commands/ai/tests/ai.test.ts b/apps/cli/commands/ai/tests/ai.test.ts
index 2fa8444bb4..76abf85dd8 100644
--- a/apps/cli/commands/ai/tests/ai.test.ts
+++ b/apps/cli/commands/ai/tests/ai.test.ts
@@ -112,11 +112,10 @@ vi.mock( 'cli/ai/sessions/recorder', () => {
 	class MockAiSessionRecorder {
 		static create = vi.fn().mockResolvedValue( new MockAiSessionRecorder() );
 		static open = vi.fn().mockResolvedValue( new MockAiSessionRecorder() );
+		async recordSdkMessage() {}
 		async recordToolProgress() {}
 		async recordSiteSelected() {}
 		async recordUserMessage() {}
-		async recordAssistantMessage() {}
-		async recordToolResult() {}
 		async recordAgentQuestion() {}
 		async recordTurnClosed() {}
 		async recordAgentSessionId() {}
@@ -133,11 +132,6 @@ vi.mock( 'cli/ai/sessions/store', () => ( {
 	deleteAiSession: vi.fn(),
 } ) );
 
-vi.mock( 'cli/ai/sessions/parser', () => ( {
-	extractAssistantMessageBlocks: vi.fn().mockReturnValue( [] ),
-	extractToolResult: vi.fn().mockReturnValue( undefined ),
-} ) );
-
 vi.mock( 'cli/ai/sessions/replay', () => ( {
 	replaySessionHistory: vi.fn(),
 } ) );
diff --git a/apps/cli/commands/ai/tests/sessions.test.ts b/apps/cli/commands/ai/tests/sessions.test.ts
index 677cb8d9ce..2a05af9a70 100644
--- a/apps/cli/commands/ai/tests/sessions.test.ts
+++ b/apps/cli/commands/ai/tests/sessions.test.ts
@@ -1,15 +1,18 @@
 import fs from 'fs/promises';
 import os from 'os';
 import path from 'path';
-import { afterEach, describe, expect, it } from 'vitest';
+import { afterEach, describe, expect, it, vi } from 'vitest';
 import { getAiSessionsDirectoryForDate, getAiSessionsRootDirectory } from 'cli/ai/sessions/paths';
 import { AiSessionRecorder } from 'cli/ai/sessions/recorder';
+import { replaySessionHistory } from 'cli/ai/sessions/replay';
 import {
 	deleteAiSession,
 	listAiSessions,
 	loadAiSession,
 	readAiSessionEventsFromFile,
 } from 'cli/ai/sessions/store';
+import type { SDKMessage } from '@anthropic-ai/claude-agent-sdk';
+import type { AiSessionEvent } from 'cli/ai/sessions/types';
 
 describe( 'ai-sessions', () => {
 	let testRoot: string | undefined;
@@ -41,14 +44,17 @@ describe( 'ai-sessions', () => {
 			source: 'prompt',
 			sitePath: '/tmp/my-wordpress-website',
 		} );
-		await recorder.recordAssistantMessage( [
-			{ type: 'text', text: 'Sure, I can help with that.' },
-			{ type: 'tool_use', name: 'Read' },
-		] );
-		await recorder.recordToolResult( {
-			ok: true,
-			text: 'File read successfully',
-		} );
+		await recorder.recordSdkMessage( {
+			type: 'assistant',
+			message: {
+				content: [
+					{
+						type: 'text',
+						text: 'Sure, I can help with that.',
+					},
+				],
+			},
+		} as SDKMessage );
 		await recorder.recordToolProgress( 'Starting process daemon…' );
 		await recorder.recordAgentQuestion( {
 			question: 'Choose a plugin slug',
@@ -83,12 +89,11 @@ describe( 'ai-sessions', () => {
 			source: 'prompt',
 			text: 'Help me create a plugin',
 		} );
-		expect( events.find( ( event ) => event.type === 'assistant.message' ) ).toMatchObject( {
-			type: 'assistant.message',
-			blocks: [
-				{ type: 'text', text: 'Sure, I can help with that.' },
-				{ type: 'tool_use', name: 'Read' },
-			],
+		expect( events.find( ( event ) => event.type === 'sdk.message' ) ).toMatchObject( {
+			type: 'sdk.message',
+			message: {
+				type: 'assistant',
+			},
 		} );
 		expect( events.find( ( event ) => event.type === 'tool.progress' ) ).toMatchObject( {
 			type: 'tool.progress',
@@ -314,4 +319,87 @@ describe( 'ai-sessions', () => {
 			older.sessionId,
 		] );
 	} );
+
+	it( 'replays raw sdk.message events', () => {
+		const ui = {
+			activeSite: null,
+			prepareForReplay: vi.fn(),
+			finishReplay: vi.fn(),
+			setReplayTimestamp: vi.fn(),
+			setActiveSite: vi.fn(),
+			beginAgentTurn: vi.fn(),
+			addUserMessage: vi.fn(),
+			handleMessage: vi.fn(),
+			setLoaderMessage: vi.fn(),
+			showAgentQuestion: vi.fn(),
+			endAgentTurn: vi.fn(),
+		};
+		const sdkAssistantMessage = {
+			type: 'assistant',
+			message: {
+				content: [
+					{
+						type: 'text',
+						text: 'hello from sdk replay',
+					},
+				],
+			},
+		};
+		const events: AiSessionEvent[] = [
+			{
+				type: 'sdk.message',
+				timestamp: '2026-03-12T10:00:01.000Z',
+				message: sdkAssistantMessage as SDKMessage,
+			},
+		];
+
+		replaySessionHistory( ui as never, events );
+
+		expect( ui.prepareForReplay ).toHaveBeenCalledTimes( 1 );
+		expect( ui.handleMessage ).toHaveBeenCalledTimes( 1 );
+		expect( ui.handleMessage ).toHaveBeenCalledWith( sdkAssistantMessage );
+		expect( ui.finishReplay ).toHaveBeenCalledTimes( 1 );
+	} );
+
+	it( 'skips ask_user echo lines during replay and starts turns on prompt messages', () => {
+		const ui = {
+			activeSite: null,
+			prepareForReplay: vi.fn(),
+			finishReplay: vi.fn(),
+			setReplayTimestamp: vi.fn(),
+			setActiveSite: vi.fn(),
+			beginAgentTurn: vi.fn(),
+			addUserMessage: vi.fn(),
+			handleMessage: vi.fn(),
+			setLoaderMessage: vi.fn(),
+			showAgentQuestion: vi.fn(),
+			endAgentTurn: vi.fn(),
+		};
+		const events: AiSessionEvent[] = [
+			{
+				type: 'user.message',
+				timestamp: '2026-03-12T11:00:00.000Z',
+				text: 'answer from ask_user',
+				source: 'ask_user',
+			},
+			{
+				type: 'user.message',
+				timestamp: '2026-03-12T11:00:01.000Z',
+				text: 'top-level prompt',
+				source: 'prompt',
+			},
+			{
+				type: 'turn.closed',
+				timestamp: '2026-03-12T11:00:02.000Z',
+				status: 'success',
+			},
+		];
+
+		replaySessionHistory( ui as never, events );
+
+		expect( ui.beginAgentTurn ).toHaveBeenCalledTimes( 1 );
+		expect( ui.addUserMessage ).toHaveBeenCalledTimes( 1 );
+		expect( ui.addUserMessage ).toHaveBeenCalledWith( 'top-level prompt' );
+		expect( ui.endAgentTurn ).toHaveBeenCalledTimes( 1 );
+	} );
 } );

From cbaa18876ef4930fe41575d388c611fd54632121 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Fri, 13 Mar 2026 00:12:38 +0100
Subject: [PATCH 20/33] Fix blinking dots in resume output

---
 apps/cli/ai/sessions/replay.ts              | 15 ++++++-
 apps/cli/ai/ui.ts                           |  4 ++
 apps/cli/commands/ai/tests/sessions.test.ts | 45 +++++++++++++++++++++
 3 files changed, 63 insertions(+), 1 deletion(-)

diff --git a/apps/cli/ai/sessions/replay.ts b/apps/cli/ai/sessions/replay.ts
index d3b567153e..bc3772f680 100644
--- a/apps/cli/ai/sessions/replay.ts
+++ b/apps/cli/ai/sessions/replay.ts
@@ -4,6 +4,7 @@ import type { AiSessionEvent } from './types';
 
 export function replaySessionHistory( ui: AiChatUI, events: AiSessionEvent[] ): void {
 	ui.prepareForReplay();
+	let isTurnOpen = false;
 
 	try {
 		for ( const event of events ) {
@@ -26,6 +27,11 @@ export function replaySessionHistory( ui: AiChatUI, events: AiSessionEvent[] ):
 					continue;
 				}
 
+				// Defensive close if the previous turn never emitted turn.closed.
+				if ( isTurnOpen ) {
+					ui.endAgentTurn();
+				}
+
 				if ( event.sitePath && ( ! ui.activeSite || ui.activeSite.path !== event.sitePath ) ) {
 					ui.setActiveSite(
 						{
@@ -37,6 +43,7 @@ export function replaySessionHistory( ui: AiChatUI, events: AiSessionEvent[] ):
 					);
 				}
 				ui.beginAgentTurn();
+				isTurnOpen = true;
 				ui.addUserMessage( event.text );
 				continue;
 			}
@@ -57,10 +64,16 @@ export function replaySessionHistory( ui: AiChatUI, events: AiSessionEvent[] ):
 			}
 
 			if ( event.type === 'turn.closed' ) {
-				ui.endAgentTurn();
+				if ( isTurnOpen ) {
+					ui.endAgentTurn();
+					isTurnOpen = false;
+				}
 			}
 		}
 	} finally {
+		if ( isTurnOpen ) {
+			ui.endAgentTurn();
+		}
 		ui.finishReplay();
 	}
 }
diff --git a/apps/cli/ai/ui.ts b/apps/cli/ai/ui.ts
index cf515a138d..5a92980a58 100644
--- a/apps/cli/ai/ui.ts
+++ b/apps/cli/ai/ui.ts
@@ -1526,6 +1526,10 @@ export class AiChatUI {
 		this.toolDotText = new Text( '\n ' + '⏺' + ' ' + toolLabel, 0, 0 );
 		this.messages.addChild( this.toolDotText );
 		this.toolDotVisible = true;
+		if ( this.replayMode ) {
+			this.tui.requestRender();
+			return;
+		}
 		this.toolDotTimer = setInterval( () => {
 			if ( ! this.toolDotText ) {
 				return;
diff --git a/apps/cli/commands/ai/tests/sessions.test.ts b/apps/cli/commands/ai/tests/sessions.test.ts
index 2a05af9a70..78bbafdda9 100644
--- a/apps/cli/commands/ai/tests/sessions.test.ts
+++ b/apps/cli/commands/ai/tests/sessions.test.ts
@@ -402,4 +402,49 @@ describe( 'ai-sessions', () => {
 		expect( ui.addUserMessage ).toHaveBeenCalledWith( 'top-level prompt' );
 		expect( ui.endAgentTurn ).toHaveBeenCalledTimes( 1 );
 	} );
+
+	it( 'closes an open replay turn when turn.closed is missing', () => {
+		const ui = {
+			activeSite: null,
+			prepareForReplay: vi.fn(),
+			finishReplay: vi.fn(),
+			setReplayTimestamp: vi.fn(),
+			setActiveSite: vi.fn(),
+			beginAgentTurn: vi.fn(),
+			addUserMessage: vi.fn(),
+			handleMessage: vi.fn(),
+			setLoaderMessage: vi.fn(),
+			showAgentQuestion: vi.fn(),
+			endAgentTurn: vi.fn(),
+		};
+		const events: AiSessionEvent[] = [
+			{
+				type: 'user.message',
+				timestamp: '2026-03-12T12:00:00.000Z',
+				text: 'top-level prompt',
+				source: 'prompt',
+			},
+			{
+				type: 'sdk.message',
+				timestamp: '2026-03-12T12:00:01.000Z',
+				message: {
+					type: 'assistant',
+					message: {
+						content: [
+							{
+								type: 'text',
+								text: 'partial response',
+							},
+						],
+					},
+				} as SDKMessage,
+			},
+		];
+
+		replaySessionHistory( ui as never, events );
+
+		expect( ui.beginAgentTurn ).toHaveBeenCalledTimes( 1 );
+		expect( ui.endAgentTurn ).toHaveBeenCalledTimes( 1 );
+		expect( ui.finishReplay ).toHaveBeenCalledTimes( 1 );
+	} );
 } );

From 3c34c7c06243babc5e0afe6e2c05f6f157d02054 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Fri, 13 Mar 2026 00:29:11 +0100
Subject: [PATCH 21/33] Save session context (cwd, model, provider)

---
 apps/cli/ai/agent.ts                        |  3 +-
 apps/cli/ai/sessions/context.ts             | 61 ++++++++++++++++
 apps/cli/ai/sessions/recorder.ts            | 16 +++++
 apps/cli/ai/sessions/types.ts               |  7 ++
 apps/cli/commands/ai/index.ts               | 21 ++++--
 apps/cli/commands/ai/tests/ai.test.ts       | 77 ++++++++++++++++++++-
 apps/cli/commands/ai/tests/sessions.test.ts | 11 +++
 7 files changed, 189 insertions(+), 7 deletions(-)
 create mode 100644 apps/cli/ai/sessions/context.ts

diff --git a/apps/cli/ai/agent.ts b/apps/cli/ai/agent.ts
index f953cae088..591167c052 100644
--- a/apps/cli/ai/agent.ts
+++ b/apps/cli/ai/agent.ts
@@ -16,6 +16,7 @@ export interface AiAgentConfig {
 	prompt: string;
 	env?: Record< string, string >;
 	model?: AiModelId;
+	cwd?: string;
 	maxTurns?: number;
 	resume?: string;
 	onAskUser?: ( questions: AskUserQuestion[] ) => Promise< Record< string, string > >;
@@ -36,7 +37,7 @@ const pathApprovalSession = createPathApprovalSession();
  * Caller can iterate messages with `for await` and call `interrupt()` to stop.
  */
 export function startAiAgent( config: AiAgentConfig ): Query {
-	const { prompt, env, model = DEFAULT_MODEL, maxTurns = 50, resume, onAskUser } = config;
+	const { prompt, env, model = DEFAULT_MODEL, cwd, maxTurns = 50, resume, onAskUser } = config;
 	const resolvedEnv = env ?? { ...( process.env as Record< string, string > ) };
 
 	return query( {
diff --git a/apps/cli/ai/sessions/context.ts b/apps/cli/ai/sessions/context.ts
new file mode 100644
index 0000000000..e95ef680b5
--- /dev/null
+++ b/apps/cli/ai/sessions/context.ts
@@ -0,0 +1,61 @@
+import { AI_MODELS, type AiModelId } from 'cli/ai/agent';
+import { AI_PROVIDERS, type AiProviderId } from 'cli/ai/providers';
+import type { LoadedAiSession } from './types';
+
+function isAiProviderId( value: string ): value is AiProviderId {
+	return Object.prototype.hasOwnProperty.call( AI_PROVIDERS, value );
+}
+
+function isAiModelId( value: string ): value is AiModelId {
+	return Object.prototype.hasOwnProperty.call( AI_MODELS, value );
+}
+
+export interface ResumeSessionContext {
+	sessionId?: string;
+	provider?: AiProviderId;
+	model?: AiModelId;
+	cwd?: string;
+}
+
+export function resolveResumeSessionContext(
+	resumeSession?: LoadedAiSession
+): ResumeSessionContext {
+	if ( ! resumeSession ) {
+		return {};
+	}
+
+	const context: ResumeSessionContext = {};
+	const linkedSessionId = resumeSession.summary.agentSessionId?.trim();
+	if ( linkedSessionId ) {
+		context.sessionId = linkedSessionId;
+	}
+
+	for ( let index = resumeSession.events.length - 1; index >= 0; index -= 1 ) {
+		const event = resumeSession.events[ index ];
+
+		if ( ! context.sessionId && event.type === 'sdk.message' ) {
+			const sessionId = ( event.message as { session_id?: unknown } ).session_id;
+			if ( typeof sessionId === 'string' && sessionId.trim().length > 0 ) {
+				context.sessionId = sessionId;
+			}
+		}
+
+		if ( event.type === 'session.context' ) {
+			if ( ! context.provider && isAiProviderId( event.provider ) ) {
+				context.provider = event.provider;
+			}
+			if ( ! context.model && isAiModelId( event.model ) ) {
+				context.model = event.model;
+			}
+			if ( ! context.cwd && event.cwd.trim().length > 0 ) {
+				context.cwd = event.cwd;
+			}
+		}
+
+		if ( context.sessionId && context.provider && context.model && context.cwd ) {
+			break;
+		}
+	}
+
+	return context;
+}
diff --git a/apps/cli/ai/sessions/recorder.ts b/apps/cli/ai/sessions/recorder.ts
index 2edbcf8789..5743b2e0bb 100644
--- a/apps/cli/ai/sessions/recorder.ts
+++ b/apps/cli/ai/sessions/recorder.ts
@@ -4,6 +4,8 @@ import path from 'path';
 import { getAiSessionsDirectoryForDate } from './paths';
 import type { AiSessionEvent, TurnStatus } from './types';
 import type { SDKMessage } from '@anthropic-ai/claude-agent-sdk';
+import type { AiModelId } from 'cli/ai/agent';
+import type { AiProviderId } from 'cli/ai/providers';
 
 function toSortableTimestampPrefix( date: Date ): string {
 	return date
@@ -74,6 +76,20 @@ export class AiSessionRecorder {
 		} );
 	}
 
+	async recordSessionContext( options: {
+		provider: AiProviderId;
+		model: AiModelId;
+		cwd: string;
+	} ): Promise< void > {
+		await this.appendEvent( {
+			type: 'session.context',
+			timestamp: toIsoTimestamp(),
+			provider: options.provider,
+			model: options.model,
+			cwd: options.cwd,
+		} );
+	}
+
 	async recordSiteSelected( site: { name: string; path: string } ): Promise< void > {
 		await this.appendEvent( {
 			type: 'site.selected',
diff --git a/apps/cli/ai/sessions/types.ts b/apps/cli/ai/sessions/types.ts
index 136ea18bb8..c68ee7b3fb 100644
--- a/apps/cli/ai/sessions/types.ts
+++ b/apps/cli/ai/sessions/types.ts
@@ -14,6 +14,13 @@ export type AiSessionEvent =
 			timestamp: string;
 			agentSessionId: string;
 	  }
+	| {
+			type: 'session.context';
+			timestamp: string;
+			provider: string;
+			model: string;
+			cwd: string;
+	  }
 	| {
 			type: 'site.selected';
 			timestamp: string;
diff --git a/apps/cli/commands/ai/index.ts b/apps/cli/commands/ai/index.ts
index 64a9ffedbd..4cf6949c3b 100644
--- a/apps/cli/commands/ai/index.ts
+++ b/apps/cli/commands/ai/index.ts
@@ -16,6 +16,7 @@ import {
 	saveSelectedAiProvider,
 } from 'cli/ai/auth';
 import { AI_PROVIDERS, type AiProviderId } from 'cli/ai/providers';
+import { resolveResumeSessionContext } from 'cli/ai/sessions/context';
 import { AiSessionRecorder } from 'cli/ai/sessions/recorder';
 import { replaySessionHistory } from 'cli/ai/sessions/replay';
 import { type LoadedAiSession, type TurnStatus } from 'cli/ai/sessions/types';
@@ -56,14 +57,19 @@ export async function runCommand(
 	options: { resumeSession?: LoadedAiSession; noSessionPersistence?: boolean } = {}
 ): Promise< void > {
 	const ui = new AiChatUI();
-	let currentProvider: AiProviderId = await resolveInitialAiProvider();
+	const resumeContext = resolveResumeSessionContext( options.resumeSession );
+	let currentProvider: AiProviderId =
+		resumeContext.provider ?? ( await resolveInitialAiProvider() );
+	let currentModel: AiModelId = resumeContext.model ?? DEFAULT_MODEL;
+	const currentWorkingDirectory = resumeContext.cwd ?? process.cwd();
 	ui.currentProvider = currentProvider;
+	ui.currentModel = currentModel;
 	ui.start();
 	ui.showWelcome();
 
 	let sessionRecorder: AiSessionRecorder | undefined;
 	let didDisableSessionPersistence = options.noSessionPersistence === true;
-	let sessionId: string | undefined = options.resumeSession?.summary.agentSessionId;
+	let sessionId: string | undefined = resumeContext.sessionId;
 	let persistQueue: Promise< void > = Promise.resolve();
 
 	if ( options.noSessionPersistence ) {
@@ -111,8 +117,6 @@ export async function runCommand(
 		void persist( ( recorder ) => recorder.recordToolProgress( message, timestamp ) );
 	} );
 
-	let currentModel: AiModelId = DEFAULT_MODEL;
-
 	ui.onSiteSelected = ( site ) => {
 		void persist( ( recorder ) =>
 			recorder.recordSiteSelected( {
@@ -244,6 +248,14 @@ export async function runCommand(
 			}]\n\n${ prompt }`;
 		}
 
+		await persist( ( recorder ) =>
+			recorder.recordSessionContext( {
+				provider: currentProvider,
+				model: currentModel,
+				cwd: currentWorkingDirectory,
+			} )
+		);
+
 		await persist( ( recorder ) =>
 			recorder.recordUserMessage( {
 				text: prompt,
@@ -256,6 +268,7 @@ export async function runCommand(
 			prompt: enrichedPrompt,
 			env,
 			model: currentModel,
+			cwd: currentWorkingDirectory,
 			resume: sessionId,
 			onAskUser: ( questions ) => askUserAndPersistAnswers( questions ),
 		} );
diff --git a/apps/cli/commands/ai/tests/ai.test.ts b/apps/cli/commands/ai/tests/ai.test.ts
index 76abf85dd8..a44f9063dd 100644
--- a/apps/cli/commands/ai/tests/ai.test.ts
+++ b/apps/cli/commands/ai/tests/ai.test.ts
@@ -1,6 +1,8 @@
 import { __ } from '@wordpress/i18n';
 import { beforeEach, describe, expect, it, vi } from 'vitest';
 import yargs from 'yargs/yargs';
+import { startAiAgent } from 'cli/ai/agent';
+import { resolveAiEnvironment, resolveInitialAiProvider } from 'cli/ai/auth';
 import { AiSessionRecorder } from 'cli/ai/sessions/recorder';
 import { deleteAiSession, listAiSessions, loadAiSession } from 'cli/ai/sessions/store';
 import { registerCommand as registerAiCommand } from 'cli/commands/ai';
@@ -10,17 +12,28 @@ import { registerCommand as registerAiSessionsResumeCommand } from 'cli/commands
 import { getAnthropicApiKey } from 'cli/lib/appdata';
 import { StudioArgv } from 'cli/types';
 
-const { reportErrorMock } = vi.hoisted( () => ( {
+const { reportErrorMock, waitForInputMock } = vi.hoisted( () => ( {
 	reportErrorMock: vi.fn(),
+	waitForInputMock: vi.fn(),
 } ) );
 
 vi.mock( 'cli/lib/appdata', () => ( {
 	getAnthropicApiKey: vi.fn(),
+	getAuthToken: vi.fn().mockResolvedValue( {
+		displayName: 'Test User',
+		email: 'test@example.com',
+	} ),
 	saveAnthropicApiKey: vi.fn(),
 } ) );
 
 vi.mock( 'cli/ai/auth', () => ( {
+	getAvailableAiProviders: vi.fn().mockResolvedValue( [ 'anthropic-api-key', 'wpcom' ] ),
+	isAiProviderReady: vi.fn().mockResolvedValue( true ),
+	prepareAiProvider: vi.fn().mockResolvedValue( undefined ),
+	resolveAiEnvironment: vi.fn().mockResolvedValue( {} ),
 	resolveInitialAiProvider: vi.fn().mockResolvedValue( 'anthropic-api-key' ),
+	resolveUnavailableAiProvider: vi.fn().mockResolvedValue( undefined ),
+	saveSelectedAiProvider: vi.fn().mockResolvedValue( undefined ),
 } ) );
 
 vi.mock( 'cli/logger', () => ( {
@@ -101,7 +114,7 @@ vi.mock( 'cli/ai/ui', () => ( {
 			return {};
 		}
 		async waitForInput() {
-			return '/exit';
+			return waitForInputMock();
 		}
 	},
 	getToolDetail: ( _name: string, input: Record< string, unknown > ) =>
@@ -114,6 +127,7 @@ vi.mock( 'cli/ai/sessions/recorder', () => {
 		static open = vi.fn().mockResolvedValue( new MockAiSessionRecorder() );
 		async recordSdkMessage() {}
 		async recordToolProgress() {}
+		async recordSessionContext() {}
 		async recordSiteSelected() {}
 		async recordUserMessage() {}
 		async recordAgentQuestion() {}
@@ -140,6 +154,7 @@ describe( 'CLI: studio ai sessions command', () => {
 	beforeEach( () => {
 		vi.clearAllMocks();
 		vi.mocked( getAnthropicApiKey ).mockResolvedValue( 'test-api-key' );
+		waitForInputMock.mockResolvedValue( '/exit' );
 		vi.spyOn( process, 'exit' ).mockImplementation( () => undefined as never );
 	} );
 
@@ -312,4 +327,62 @@ describe( 'CLI: studio ai sessions command', () => {
 		expect( deleteAiSession ).not.toHaveBeenCalled();
 		expect( reportErrorMock ).toHaveBeenCalled();
 	} );
+
+	it( 'restores provider, model, cwd, and resume session id from session events', async () => {
+		vi.mocked( resolveInitialAiProvider ).mockResolvedValue( 'wpcom' );
+		waitForInputMock.mockResolvedValueOnce( 'Continue the task' ).mockResolvedValueOnce( '/exit' );
+
+		vi.mocked( listAiSessions ).mockResolvedValue( [
+			{
+				id: 'session-latest',
+				filePath: '/tmp/session-latest.jsonl',
+				createdAt: '2026-03-11T11:00:00.000Z',
+				updatedAt: '2026-03-11T11:00:00.000Z',
+				linkedAgentSessionIds: [],
+				eventCount: 2,
+			},
+		] );
+		vi.mocked( loadAiSession ).mockResolvedValue( {
+			summary: {
+				id: 'session-latest',
+				filePath: '/tmp/session-latest.jsonl',
+				createdAt: '2026-03-11T11:00:00.000Z',
+				updatedAt: '2026-03-11T11:00:00.000Z',
+				linkedAgentSessionIds: [],
+				eventCount: 2,
+			},
+			events: [
+				{
+					type: 'session.context',
+					timestamp: '2026-03-11T11:00:00.000Z',
+					provider: 'anthropic-api-key',
+					model: 'claude-opus-4-6',
+					cwd: '/tmp/resume-cwd',
+				},
+				{
+					type: 'sdk.message',
+					timestamp: '2026-03-11T11:00:01.000Z',
+					message: {
+						type: 'assistant',
+						session_id: 'session-from-sdk-message',
+						message: {
+							content: [],
+						},
+					},
+				},
+			],
+		} );
+
+		await buildParser().parseAsync( [ 'ai', 'sessions', 'resume', 'latest' ] );
+
+		expect( resolveAiEnvironment ).toHaveBeenCalledWith( 'anthropic-api-key' );
+		expect( startAiAgent ).toHaveBeenCalledWith(
+			expect.objectContaining( {
+				model: 'claude-opus-4-6',
+				cwd: '/tmp/resume-cwd',
+				resume: 'session-from-sdk-message',
+			} )
+		);
+		expect( process.exit ).toHaveBeenCalledWith( 0 );
+	} );
 } );
diff --git a/apps/cli/commands/ai/tests/sessions.test.ts b/apps/cli/commands/ai/tests/sessions.test.ts
index 78bbafdda9..9f76e1e601 100644
--- a/apps/cli/commands/ai/tests/sessions.test.ts
+++ b/apps/cli/commands/ai/tests/sessions.test.ts
@@ -44,6 +44,11 @@ describe( 'ai-sessions', () => {
 			source: 'prompt',
 			sitePath: '/tmp/my-wordpress-website',
 		} );
+		await recorder.recordSessionContext( {
+			provider: 'anthropic-api-key',
+			model: 'claude-sonnet-4-6',
+			cwd: '/tmp/my-wordpress-website',
+		} );
 		await recorder.recordSdkMessage( {
 			type: 'assistant',
 			message: {
@@ -95,6 +100,12 @@ describe( 'ai-sessions', () => {
 				type: 'assistant',
 			},
 		} );
+		expect( events.find( ( event ) => event.type === 'session.context' ) ).toMatchObject( {
+			type: 'session.context',
+			provider: 'anthropic-api-key',
+			model: 'claude-sonnet-4-6',
+			cwd: '/tmp/my-wordpress-website',
+		} );
 		expect( events.find( ( event ) => event.type === 'tool.progress' ) ).toMatchObject( {
 			type: 'tool.progress',
 			message: 'Starting process daemon…',

From c64473429e4211f1aec4e5efcc5d30bb1e194961 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Fri, 13 Mar 2026 08:34:12 +0100
Subject: [PATCH 22/33] Extract sessions filename related methods to
 file-naming.ts

---
 apps/cli/ai/sessions/file-naming.ts | 37 +++++++++++++++++++++++++++++
 apps/cli/ai/sessions/recorder.ts    | 10 ++------
 apps/cli/ai/sessions/summary.ts     | 12 ++--------
 3 files changed, 41 insertions(+), 18 deletions(-)
 create mode 100644 apps/cli/ai/sessions/file-naming.ts

diff --git a/apps/cli/ai/sessions/file-naming.ts b/apps/cli/ai/sessions/file-naming.ts
new file mode 100644
index 0000000000..6e63dbeb24
--- /dev/null
+++ b/apps/cli/ai/sessions/file-naming.ts
@@ -0,0 +1,37 @@
+import path from 'path';
+
+const SESSION_FILE_EXTENSION = '.jsonl';
+const SESSION_ID_REGEX = /\b([0-9a-f]{8}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{12})\b/i;
+
+/**
+ * Session files follow this stable naming contract:
+ * `<iso8601-filename-timestamp>-<session-uuid>.jsonl`
+ *
+ * Example:
+ * `2026-03-11T10-00-00-8b4cead7-3f8b-4727-86cd-a495c055850a.jsonl`
+ *
+ * Why this format:
+ * - The ISO-8601-derived timestamp prefix keeps files lexicographically sortable by start time.
+ * - `:` is replaced with `-` so filenames are valid on Windows.
+ * - UUID suffix guarantees uniqueness for sessions started in the same second.
+ */
+export function buildAiSessionFileName( startedAt: Date, sessionId: string ): string {
+	const sortableTimestamp = startedAt
+		.toISOString()
+		.replace( /:/g, '-' )
+		.replace( /\.\d{3}Z$/, '' );
+	return `${ sortableTimestamp }-${ sessionId }${ SESSION_FILE_EXTENSION }`;
+}
+
+/**
+ * Reads the canonical session id from a session file path produced by
+ * `buildAiSessionFileName()`.
+ *
+ * If the file does not match the expected contract, we fall back to the bare
+ * filename (without extension) so older/unexpected files remain listable.
+ */
+export function extractAiSessionIdFromFilePath( filePath: string ): string {
+	const fileName = path.basename( filePath, SESSION_FILE_EXTENSION );
+	const uuidMatch = fileName.match( SESSION_ID_REGEX );
+	return uuidMatch?.[ 1 ] ?? fileName;
+}
diff --git a/apps/cli/ai/sessions/recorder.ts b/apps/cli/ai/sessions/recorder.ts
index 5743b2e0bb..80a1d37e09 100644
--- a/apps/cli/ai/sessions/recorder.ts
+++ b/apps/cli/ai/sessions/recorder.ts
@@ -1,19 +1,13 @@
 import crypto from 'crypto';
 import fs from 'fs/promises';
 import path from 'path';
+import { buildAiSessionFileName } from './file-naming';
 import { getAiSessionsDirectoryForDate } from './paths';
 import type { AiSessionEvent, TurnStatus } from './types';
 import type { SDKMessage } from '@anthropic-ai/claude-agent-sdk';
 import type { AiModelId } from 'cli/ai/agent';
 import type { AiProviderId } from 'cli/ai/providers';
 
-function toSortableTimestampPrefix( date: Date ): string {
-	return date
-		.toISOString()
-		.replace( /:/g, '-' )
-		.replace( /\.\d{3}Z$/, '' );
-}
-
 function toIsoTimestamp( value?: Date ): string {
 	return ( value ?? new Date() ).toISOString();
 }
@@ -34,7 +28,7 @@ export class AiSessionRecorder {
 		const startedAt = options.startedAt ?? new Date();
 		const sessionId = crypto.randomUUID();
 		const directory = getAiSessionsDirectoryForDate( startedAt );
-		const fileName = `${ toSortableTimestampPrefix( startedAt ) }-${ sessionId }.jsonl`;
+		const fileName = buildAiSessionFileName( startedAt, sessionId );
 		const filePath = path.join( directory, fileName );
 
 		await fs.mkdir( directory, { recursive: true } );
diff --git a/apps/cli/ai/sessions/summary.ts b/apps/cli/ai/sessions/summary.ts
index 9a2ba8a643..f613e63e87 100644
--- a/apps/cli/ai/sessions/summary.ts
+++ b/apps/cli/ai/sessions/summary.ts
@@ -1,15 +1,7 @@
 import fs from 'fs/promises';
-import path from 'path';
+import { extractAiSessionIdFromFilePath } from './file-naming';
 import type { AiSessionEvent, AiSessionSummary } from './types';
 
-function getSessionIdFromPath( filePath: string ): string {
-	const fileName = path.basename( filePath, '.jsonl' );
-	const uuidMatch = fileName.match(
-		/\b([0-9a-f]{8}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{12})\b/i
-	);
-	return uuidMatch?.[ 1 ] ?? fileName;
-}
-
 export async function readAiSessionSummaryFromEvents(
 	filePath: string,
 	events: AiSessionEvent[]
@@ -21,7 +13,7 @@ export async function readAiSessionSummaryFromEvents(
 	const linkedAgentSessionIds: string[] = [];
 	let createdAt: string | undefined;
 	let updatedAt: string | undefined;
-	let sessionId = getSessionIdFromPath( filePath );
+	let sessionId = extractAiSessionIdFromFilePath( filePath );
 	let firstPrompt: string | undefined;
 	let selectedSiteName: string | undefined;
 	let endReason: 'error' | 'stopped' | undefined;

From 6f77f78a5414964e4dabf08c45edf69e70cf6ff9 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Fri, 13 Mar 2026 08:40:39 +0100
Subject: [PATCH 23/33] Clarify ai sessions path helpers

---
 apps/cli/ai/sessions/paths.ts | 2 ++
 1 file changed, 2 insertions(+)

diff --git a/apps/cli/ai/sessions/paths.ts b/apps/cli/ai/sessions/paths.ts
index da69fb1796..5570d19bfa 100644
--- a/apps/cli/ai/sessions/paths.ts
+++ b/apps/cli/ai/sessions/paths.ts
@@ -1,6 +1,7 @@
 import path from 'path';
 import { getAppdataDirectory } from 'cli/lib/appdata';
 
+// Keep month/day segments zero-padded so directory names sort chronologically.
 function formatDatePart( value: number ): string {
 	return String( value ).padStart( 2, '0' );
 }
@@ -9,6 +10,7 @@ export function getAiSessionsRootDirectory(): string {
 	return path.join( getAppdataDirectory(), 'sessions' );
 }
 
+// Bucket sessions by local calendar date: <root>/<YYYY>/<MM>/<DD>.
 export function getAiSessionsDirectoryForDate( date: Date ): string {
 	const year = String( date.getFullYear() );
 	const month = formatDatePart( date.getMonth() + 1 );

From 7d4c2d32d3fb644f76976dc540e0e2db0975f897 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Fri, 13 Mar 2026 13:17:04 +0100
Subject: [PATCH 24/33] Restore _activeSiteData from _activeSite when not set

---
 apps/cli/ai/tests/ui.test.ts | 56 ++++++++++++++++++++++++++++++++++++
 apps/cli/ai/ui.ts            | 12 ++++++--
 2 files changed, 66 insertions(+), 2 deletions(-)
 create mode 100644 apps/cli/ai/tests/ui.test.ts

diff --git a/apps/cli/ai/tests/ui.test.ts b/apps/cli/ai/tests/ui.test.ts
new file mode 100644
index 0000000000..f1d8fcde95
--- /dev/null
+++ b/apps/cli/ai/tests/ui.test.ts
@@ -0,0 +1,56 @@
+import { beforeEach, describe, expect, it, vi } from 'vitest';
+import { AiChatUI } from 'cli/ai/ui';
+import { getSiteUrl, readAppdata } from 'cli/lib/appdata';
+import { openBrowser } from 'cli/lib/browser';
+
+vi.mock( 'cli/lib/appdata', async ( importOriginal ) => {
+	const actual = await importOriginal< typeof import('cli/lib/appdata') >();
+	return {
+		...actual,
+		readAppdata: vi.fn(),
+		getSiteUrl: vi.fn(),
+	};
+} );
+
+vi.mock( 'cli/lib/browser', () => ( {
+	openBrowser: vi.fn(),
+} ) );
+
+describe( 'AiChatUI.openActiveSiteInBrowser', () => {
+	beforeEach( () => {
+		vi.clearAllMocks();
+	} );
+
+	it( 'opens the restored active site when activeSiteData is missing', async () => {
+		const restoredSite = {
+			name: 'my-site',
+			path: '/Users/test/Studio/my-site',
+			running: false,
+		};
+
+		const siteData = {
+			name: 'my-site',
+			path: '/Users/test/Studio/my-site',
+			port: 8080,
+		};
+
+		const ui = Object.create( AiChatUI.prototype ) as {
+			openActiveSiteInBrowser: () => Promise< boolean >;
+			[ key: string ]: unknown;
+		};
+		ui._activeSite = restoredSite;
+		ui._activeSiteData = null;
+
+		vi.mocked( readAppdata ).mockResolvedValue( {
+			sites: [ siteData ],
+		} as never );
+		vi.mocked( getSiteUrl ).mockReturnValue( 'http://localhost:8080' );
+
+		const opened = await ui.openActiveSiteInBrowser();
+
+		expect( opened ).toBe( true );
+		expect( readAppdata ).toHaveBeenCalledTimes( 1 );
+		expect( openBrowser ).toHaveBeenCalledWith( 'http://localhost:8080' );
+		expect( ui._activeSiteData ).toEqual( siteData );
+	} );
+} );
diff --git a/apps/cli/ai/ui.ts b/apps/cli/ai/ui.ts
index 5a92980a58..ef2e917b02 100644
--- a/apps/cli/ai/ui.ts
+++ b/apps/cli/ai/ui.ts
@@ -1111,13 +1111,21 @@ export class AiChatUI {
 			await openBrowser( this._activeSite.url );
 			return true;
 		}
-		if ( ! this._activeSiteData ) {
+		if ( ! this._activeSite && ! this._activeSiteData ) {
 			return false;
 		}
 		// Re-read appdata to get the current site state (port/domain may have changed)
 		const appdata = await readAppdata();
-		const freshSiteData = appdata.sites?.find( ( s ) => s.name === this._activeSite?.name );
+		const activeSiteName = this._activeSite?.name ?? this._activeSiteData?.name;
+		const freshSiteData = appdata.sites?.find( ( site ) => site.name === activeSiteName );
 		const siteData = freshSiteData ?? this._activeSiteData;
+		if ( siteData ) {
+			this._activeSiteData = siteData;
+		}
+		if ( ! siteData ) {
+			return false;
+		}
+
 		const url = getSiteUrl( siteData );
 		if ( url ) {
 			await openBrowser( url );

From ed5de4bfce8fdd2d744a972215a66eabecd4ed2b Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Fri, 13 Mar 2026 13:32:25 +0100
Subject: [PATCH 25/33] Ensure sessions are only recorded when persist is
 called

---
 apps/cli/commands/ai/index.ts         | 20 ++++++++++++++++----
 apps/cli/commands/ai/tests/ai.test.ts | 23 ++++++++++++++++-------
 2 files changed, 32 insertions(+), 11 deletions(-)

diff --git a/apps/cli/commands/ai/index.ts b/apps/cli/commands/ai/index.ts
index 4cf6949c3b..bdcbcfc617 100644
--- a/apps/cli/commands/ai/index.ts
+++ b/apps/cli/commands/ai/index.ts
@@ -74,7 +74,16 @@ export async function runCommand(
 
 	if ( options.noSessionPersistence ) {
 		ui.showInfo( 'Session persistence disabled (--no-session-persistence).' );
-	} else {
+	}
+
+	const ensureSessionRecorder = async (): Promise< AiSessionRecorder | undefined > => {
+		if ( didDisableSessionPersistence ) {
+			return undefined;
+		}
+		if ( sessionRecorder ) {
+			return sessionRecorder;
+		}
+
 		try {
 			if ( options.resumeSession ) {
 				sessionRecorder = await AiSessionRecorder.open( {
@@ -89,16 +98,19 @@ export async function runCommand(
 			didDisableSessionPersistence = true;
 			ui.showError( `Session persistence disabled: ${ getErrorMessage( error ) }` );
 		}
-	}
+
+		return sessionRecorder;
+	};
 
 	const persist = ( callback: ( recorder: AiSessionRecorder ) => Promise< void > ) => {
 		persistQueue = persistQueue.then( async () => {
-			if ( ! sessionRecorder ) {
+			const recorder = await ensureSessionRecorder();
+			if ( ! recorder ) {
 				return;
 			}
 
 			try {
-				await callback( sessionRecorder );
+				await callback( recorder );
 			} catch ( error ) {
 				sessionRecorder = undefined;
 				if ( ! didDisableSessionPersistence ) {
diff --git a/apps/cli/commands/ai/tests/ai.test.ts b/apps/cli/commands/ai/tests/ai.test.ts
index a44f9063dd..b26b1ab5c7 100644
--- a/apps/cli/commands/ai/tests/ai.test.ts
+++ b/apps/cli/commands/ai/tests/ai.test.ts
@@ -184,7 +184,15 @@ describe( 'CLI: studio ai sessions command', () => {
 		return parser;
 	}
 
-	it( 'records sessions by default when running studio ai', async () => {
+	it( 'does not record an empty session when running studio ai and exiting immediately', async () => {
+		await buildParser().parseAsync( [ 'ai' ] );
+
+		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).create ).not.toHaveBeenCalled();
+	} );
+
+	it( 'records sessions by default once a prompt is submitted', async () => {
+		waitForInputMock.mockResolvedValueOnce( 'Hello' ).mockResolvedValueOnce( '/exit' );
+
 		await buildParser().parseAsync( [ 'ai' ] );
 
 		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).create ).toHaveBeenCalledTimes( 1 );
@@ -231,12 +239,7 @@ describe( 'CLI: studio ai sessions command', () => {
 		await buildParser().parseAsync( [ 'ai', 'sessions', 'resume', 'latest' ] );
 
 		expect( loadAiSession ).toHaveBeenCalledWith( 'session-latest' );
-		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).open ).toHaveBeenCalledWith(
-			expect.objectContaining( {
-				sessionId: 'session-latest',
-				filePath: '/tmp/session-latest.jsonl',
-			} )
-		);
+		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).open ).not.toHaveBeenCalled();
 		expect( process.exit ).toHaveBeenCalledWith( 0 );
 	} );
 
@@ -376,6 +379,12 @@ describe( 'CLI: studio ai sessions command', () => {
 		await buildParser().parseAsync( [ 'ai', 'sessions', 'resume', 'latest' ] );
 
 		expect( resolveAiEnvironment ).toHaveBeenCalledWith( 'anthropic-api-key' );
+		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).open ).toHaveBeenCalledWith(
+			expect.objectContaining( {
+				sessionId: 'session-latest',
+				filePath: '/tmp/session-latest.jsonl',
+			} )
+		);
 		expect( startAiAgent ).toHaveBeenCalledWith(
 			expect.objectContaining( {
 				model: 'claude-opus-4-6',

From 59acf9e7ed3f23344bfe6a37917e50a6b8823f5b Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Tue, 17 Mar 2026 11:09:17 +0100
Subject: [PATCH 26/33] Update AI sessions commands registration

---
 apps/cli/index.ts | 34 ++++++++++++++++++++++++++++++++--
 1 file changed, 32 insertions(+), 2 deletions(-)

diff --git a/apps/cli/index.ts b/apps/cli/index.ts
index 3004d9a839..43e9cf1b11 100644
--- a/apps/cli/index.ts
+++ b/apps/cli/index.ts
@@ -157,8 +157,38 @@ async function main() {
 		.strict();
 
 	if ( __ENABLE_STUDIO_AI__ ) {
-		const { registerCommand: registerAiCommand } = await import( 'cli/commands/ai' );
-		registerAiCommand( studioArgv );
+		studioArgv.command( 'ai', __( 'AI-powered WordPress assistant' ), async ( aiYargs ) => {
+			const { registerCommand: registerAiCommand } = await import( 'cli/commands/ai' );
+			registerAiCommand( aiYargs );
+			aiYargs.command( 'sessions', __( 'Manage AI sessions' ), async ( sessionsYargs ) => {
+				const [
+					{ registerCommand: registerAiSessionsListCommand },
+					{ registerCommand: registerAiSessionsResumeCommand },
+					{ registerCommand: registerAiSessionsDeleteCommand },
+				] = await Promise.all( [
+					import( 'cli/commands/ai/sessions/list' ),
+					import( 'cli/commands/ai/sessions/resume' ),
+					import( 'cli/commands/ai/sessions/delete' ),
+				] );
+
+				sessionsYargs
+					.option( 'path', {
+						hidden: true,
+					} )
+					.option( 'session-persistence', {
+						type: 'boolean',
+						default: true,
+						description: __( 'Record this AI chat session to disk' ),
+					} );
+				registerAiSessionsListCommand( sessionsYargs );
+				registerAiSessionsResumeCommand( sessionsYargs );
+				registerAiSessionsDeleteCommand( sessionsYargs );
+				sessionsYargs
+					.version( false )
+					.demandCommand( 1, __( 'You must provide a valid ai sessions command' ) );
+			} );
+			aiYargs.version( false );
+		} );
 	}
 	if ( __ENABLE_AGENT_SUITE__ ) {
 		const { registerCommand: registerMcpCommand } = await import( 'cli/commands/mcp' );

From 2de5ec1fd7502723f30cd2d3d9273b79684c797d Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Tue, 17 Mar 2026 11:09:40 +0100
Subject: [PATCH 27/33] Use truncateToWidth and visibleWidth from pi-tui

---
 apps/cli/commands/ai/sessions/helpers.ts | 14 +++++---------
 1 file changed, 5 insertions(+), 9 deletions(-)

diff --git a/apps/cli/commands/ai/sessions/helpers.ts b/apps/cli/commands/ai/sessions/helpers.ts
index 5ef90b556e..b34678ec70 100644
--- a/apps/cli/commands/ai/sessions/helpers.ts
+++ b/apps/cli/commands/ai/sessions/helpers.ts
@@ -1,4 +1,5 @@
 import { select } from '@inquirer/prompts';
+import { truncateToWidth, visibleWidth } from '@mariozechner/pi-tui';
 import { __ } from '@wordpress/i18n';
 import chalk from 'chalk';
 import { listAiSessions } from 'cli/ai/sessions/store';
@@ -47,19 +48,14 @@ function toSingleLine( text: string ): string {
 }
 
 function truncateWithEllipsis( text: string, maxLength: number ): string {
-	if ( text.length <= maxLength ) {
-		return text;
+	if ( maxLength <= 0 ) {
+		return '';
 	}
-
-	if ( maxLength <= 1 ) {
+	if ( maxLength === 1 ) {
 		return '…';
 	}
 
-	return text.slice( 0, maxLength - 1 ) + '…';
-}
-
-function visibleWidth( text: string ): number {
-	return Array.from( text ).length;
+	return truncateToWidth( text, maxLength, '…' );
 }
 
 function padEndVisible( text: string, width: number ): string {

From 9fab1158331ecb075141a7a778c3dc08a252b790 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Tue, 17 Mar 2026 16:00:55 +0100
Subject: [PATCH 28/33] Stop persisting cwd in session context

---
 apps/cli/ai/agent.ts                        | 2 +-
 apps/cli/ai/sessions/context.ts             | 6 +-----
 apps/cli/ai/sessions/recorder.ts            | 2 --
 apps/cli/ai/sessions/types.ts               | 1 -
 apps/cli/commands/ai/index.ts               | 3 ---
 apps/cli/commands/ai/tests/ai.test.ts       | 4 +---
 apps/cli/commands/ai/tests/sessions.test.ts | 2 --
 7 files changed, 3 insertions(+), 17 deletions(-)

diff --git a/apps/cli/ai/agent.ts b/apps/cli/ai/agent.ts
index 591167c052..4f971e61d8 100644
--- a/apps/cli/ai/agent.ts
+++ b/apps/cli/ai/agent.ts
@@ -37,7 +37,7 @@ const pathApprovalSession = createPathApprovalSession();
  * Caller can iterate messages with `for await` and call `interrupt()` to stop.
  */
 export function startAiAgent( config: AiAgentConfig ): Query {
-	const { prompt, env, model = DEFAULT_MODEL, cwd, maxTurns = 50, resume, onAskUser } = config;
+	const { prompt, env, model = DEFAULT_MODEL, maxTurns = 50, resume, onAskUser } = config;
 	const resolvedEnv = env ?? { ...( process.env as Record< string, string > ) };
 
 	return query( {
diff --git a/apps/cli/ai/sessions/context.ts b/apps/cli/ai/sessions/context.ts
index e95ef680b5..72f787d2a7 100644
--- a/apps/cli/ai/sessions/context.ts
+++ b/apps/cli/ai/sessions/context.ts
@@ -14,7 +14,6 @@ export interface ResumeSessionContext {
 	sessionId?: string;
 	provider?: AiProviderId;
 	model?: AiModelId;
-	cwd?: string;
 }
 
 export function resolveResumeSessionContext(
@@ -47,12 +46,9 @@ export function resolveResumeSessionContext(
 			if ( ! context.model && isAiModelId( event.model ) ) {
 				context.model = event.model;
 			}
-			if ( ! context.cwd && event.cwd.trim().length > 0 ) {
-				context.cwd = event.cwd;
-			}
 		}
 
-		if ( context.sessionId && context.provider && context.model && context.cwd ) {
+		if ( context.sessionId && context.provider && context.model ) {
 			break;
 		}
 	}
diff --git a/apps/cli/ai/sessions/recorder.ts b/apps/cli/ai/sessions/recorder.ts
index 80a1d37e09..1054cd9844 100644
--- a/apps/cli/ai/sessions/recorder.ts
+++ b/apps/cli/ai/sessions/recorder.ts
@@ -73,14 +73,12 @@ export class AiSessionRecorder {
 	async recordSessionContext( options: {
 		provider: AiProviderId;
 		model: AiModelId;
-		cwd: string;
 	} ): Promise< void > {
 		await this.appendEvent( {
 			type: 'session.context',
 			timestamp: toIsoTimestamp(),
 			provider: options.provider,
 			model: options.model,
-			cwd: options.cwd,
 		} );
 	}
 
diff --git a/apps/cli/ai/sessions/types.ts b/apps/cli/ai/sessions/types.ts
index c68ee7b3fb..4b4f02276d 100644
--- a/apps/cli/ai/sessions/types.ts
+++ b/apps/cli/ai/sessions/types.ts
@@ -19,7 +19,6 @@ export type AiSessionEvent =
 			timestamp: string;
 			provider: string;
 			model: string;
-			cwd: string;
 	  }
 	| {
 			type: 'site.selected';
diff --git a/apps/cli/commands/ai/index.ts b/apps/cli/commands/ai/index.ts
index bdcbcfc617..deeb840ac4 100644
--- a/apps/cli/commands/ai/index.ts
+++ b/apps/cli/commands/ai/index.ts
@@ -61,7 +61,6 @@ export async function runCommand(
 	let currentProvider: AiProviderId =
 		resumeContext.provider ?? ( await resolveInitialAiProvider() );
 	let currentModel: AiModelId = resumeContext.model ?? DEFAULT_MODEL;
-	const currentWorkingDirectory = resumeContext.cwd ?? process.cwd();
 	ui.currentProvider = currentProvider;
 	ui.currentModel = currentModel;
 	ui.start();
@@ -264,7 +263,6 @@ export async function runCommand(
 			recorder.recordSessionContext( {
 				provider: currentProvider,
 				model: currentModel,
-				cwd: currentWorkingDirectory,
 			} )
 		);
 
@@ -280,7 +278,6 @@ export async function runCommand(
 			prompt: enrichedPrompt,
 			env,
 			model: currentModel,
-			cwd: currentWorkingDirectory,
 			resume: sessionId,
 			onAskUser: ( questions ) => askUserAndPersistAnswers( questions ),
 		} );
diff --git a/apps/cli/commands/ai/tests/ai.test.ts b/apps/cli/commands/ai/tests/ai.test.ts
index b26b1ab5c7..c157b1627d 100644
--- a/apps/cli/commands/ai/tests/ai.test.ts
+++ b/apps/cli/commands/ai/tests/ai.test.ts
@@ -331,7 +331,7 @@ describe( 'CLI: studio ai sessions command', () => {
 		expect( reportErrorMock ).toHaveBeenCalled();
 	} );
 
-	it( 'restores provider, model, cwd, and resume session id from session events', async () => {
+	it( 'restores provider, model, and resume session id from session events', async () => {
 		vi.mocked( resolveInitialAiProvider ).mockResolvedValue( 'wpcom' );
 		waitForInputMock.mockResolvedValueOnce( 'Continue the task' ).mockResolvedValueOnce( '/exit' );
 
@@ -360,7 +360,6 @@ describe( 'CLI: studio ai sessions command', () => {
 					timestamp: '2026-03-11T11:00:00.000Z',
 					provider: 'anthropic-api-key',
 					model: 'claude-opus-4-6',
-					cwd: '/tmp/resume-cwd',
 				},
 				{
 					type: 'sdk.message',
@@ -388,7 +387,6 @@ describe( 'CLI: studio ai sessions command', () => {
 		expect( startAiAgent ).toHaveBeenCalledWith(
 			expect.objectContaining( {
 				model: 'claude-opus-4-6',
-				cwd: '/tmp/resume-cwd',
 				resume: 'session-from-sdk-message',
 			} )
 		);
diff --git a/apps/cli/commands/ai/tests/sessions.test.ts b/apps/cli/commands/ai/tests/sessions.test.ts
index 9f76e1e601..ab82505621 100644
--- a/apps/cli/commands/ai/tests/sessions.test.ts
+++ b/apps/cli/commands/ai/tests/sessions.test.ts
@@ -47,7 +47,6 @@ describe( 'ai-sessions', () => {
 		await recorder.recordSessionContext( {
 			provider: 'anthropic-api-key',
 			model: 'claude-sonnet-4-6',
-			cwd: '/tmp/my-wordpress-website',
 		} );
 		await recorder.recordSdkMessage( {
 			type: 'assistant',
@@ -104,7 +103,6 @@ describe( 'ai-sessions', () => {
 			type: 'session.context',
 			provider: 'anthropic-api-key',
 			model: 'claude-sonnet-4-6',
-			cwd: '/tmp/my-wordpress-website',
 		} );
 		expect( events.find( ( event ) => event.type === 'tool.progress' ) ).toMatchObject( {
 			type: 'tool.progress',

From f59b43a0f5ab38273c011c91620d45f118f2ad97 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Wed, 18 Mar 2026 10:45:11 +0100
Subject: [PATCH 29/33] Save remote and url to site.selected event

---
 apps/cli/ai/sessions/recorder.ts            |  9 ++-
 apps/cli/ai/sessions/replay.ts              |  2 +
 apps/cli/ai/sessions/types.ts               |  2 +
 apps/cli/commands/ai/index.ts               |  2 +
 apps/cli/commands/ai/tests/sessions.test.ts | 62 +++++++++++++++++++++
 5 files changed, 76 insertions(+), 1 deletion(-)

diff --git a/apps/cli/ai/sessions/recorder.ts b/apps/cli/ai/sessions/recorder.ts
index 1054cd9844..b0aa422d2e 100644
--- a/apps/cli/ai/sessions/recorder.ts
+++ b/apps/cli/ai/sessions/recorder.ts
@@ -82,12 +82,19 @@ export class AiSessionRecorder {
 		} );
 	}
 
-	async recordSiteSelected( site: { name: string; path: string } ): Promise< void > {
+	async recordSiteSelected( site: {
+		name: string;
+		path: string;
+		remote?: boolean;
+		url?: string;
+	} ): Promise< void > {
 		await this.appendEvent( {
 			type: 'site.selected',
 			timestamp: toIsoTimestamp(),
 			siteName: site.name,
 			sitePath: site.path,
+			remote: site.remote,
+			url: site.url,
 		} );
 	}
 
diff --git a/apps/cli/ai/sessions/replay.ts b/apps/cli/ai/sessions/replay.ts
index bc3772f680..e8a6751e5f 100644
--- a/apps/cli/ai/sessions/replay.ts
+++ b/apps/cli/ai/sessions/replay.ts
@@ -16,6 +16,8 @@ export function replaySessionHistory( ui: AiChatUI, events: AiSessionEvent[] ):
 						name: event.siteName,
 						path: event.sitePath,
 						running: false,
+						remote: event.remote === true,
+						url: typeof event.url === 'string' ? event.url : undefined,
 					},
 					{ announce: false, emitEvent: false }
 				);
diff --git a/apps/cli/ai/sessions/types.ts b/apps/cli/ai/sessions/types.ts
index 4b4f02276d..5bd38f7e7a 100644
--- a/apps/cli/ai/sessions/types.ts
+++ b/apps/cli/ai/sessions/types.ts
@@ -25,6 +25,8 @@ export type AiSessionEvent =
 			timestamp: string;
 			siteName: string;
 			sitePath: string;
+			remote?: boolean;
+			url?: string;
 	  }
 	| {
 			type: 'user.message';
diff --git a/apps/cli/commands/ai/index.ts b/apps/cli/commands/ai/index.ts
index deeb840ac4..aff6c2fa78 100644
--- a/apps/cli/commands/ai/index.ts
+++ b/apps/cli/commands/ai/index.ts
@@ -133,6 +133,8 @@ export async function runCommand(
 			recorder.recordSiteSelected( {
 				name: site.name,
 				path: site.path,
+				remote: site.remote,
+				url: site.url,
 			} )
 		);
 	};
diff --git a/apps/cli/commands/ai/tests/sessions.test.ts b/apps/cli/commands/ai/tests/sessions.test.ts
index ab82505621..77cb02e69e 100644
--- a/apps/cli/commands/ai/tests/sessions.test.ts
+++ b/apps/cli/commands/ai/tests/sessions.test.ts
@@ -144,6 +144,29 @@ describe( 'ai-sessions', () => {
 		] );
 	} );
 
+	it( 'persists remote site metadata in site.selected events', async () => {
+		testRoot = await fs.mkdtemp( path.join( os.tmpdir(), 'studio-ai-sessions-' ) );
+		process.env.E2E = '1';
+		process.env.E2E_APP_DATA_PATH = testRoot;
+
+		const recorder = await AiSessionRecorder.create();
+		await recorder.recordSiteSelected( {
+			name: 'my-remote-site',
+			path: '',
+			remote: true,
+			url: 'https://my-remote-site.wordpress.com',
+		} );
+
+		const events = await readAiSessionEventsFromFile( recorder.filePath );
+		expect( events.find( ( event ) => event.type === 'site.selected' ) ).toMatchObject( {
+			type: 'site.selected',
+			siteName: 'my-remote-site',
+			sitePath: '',
+			remote: true,
+			url: 'https://my-remote-site.wordpress.com',
+		} );
+	} );
+
 	it( 'loads sessions by id prefix with linked Claude session metadata', async () => {
 		testRoot = await fs.mkdtemp( path.join( os.tmpdir(), 'studio-ai-sessions-' ) );
 		process.env.E2E = '1';
@@ -456,4 +479,43 @@ describe( 'ai-sessions', () => {
 		expect( ui.endAgentTurn ).toHaveBeenCalledTimes( 1 );
 		expect( ui.finishReplay ).toHaveBeenCalledTimes( 1 );
 	} );
+
+	it( 'replays remote site metadata from site.selected events', () => {
+		const ui = {
+			activeSite: null,
+			prepareForReplay: vi.fn(),
+			finishReplay: vi.fn(),
+			setReplayTimestamp: vi.fn(),
+			setActiveSite: vi.fn(),
+			beginAgentTurn: vi.fn(),
+			addUserMessage: vi.fn(),
+			handleMessage: vi.fn(),
+			setLoaderMessage: vi.fn(),
+			showAgentQuestion: vi.fn(),
+			endAgentTurn: vi.fn(),
+		};
+		const events: AiSessionEvent[] = [
+			{
+				type: 'site.selected',
+				timestamp: '2026-03-12T13:00:00.000Z',
+				siteName: 'my-remote-site',
+				sitePath: '',
+				remote: true,
+				url: 'https://my-remote-site.wordpress.com',
+			},
+		];
+
+		replaySessionHistory( ui as never, events );
+
+		expect( ui.setActiveSite ).toHaveBeenCalledWith(
+			{
+				name: 'my-remote-site',
+				path: '',
+				running: false,
+				remote: true,
+				url: 'https://my-remote-site.wordpress.com',
+			},
+			{ announce: false, emitEvent: false }
+		);
+	} );
 } );

From ffb4ad92aafe511c1f83522e1564b2960db78bc7 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Thu, 19 Mar 2026 16:49:42 +0100
Subject: [PATCH 30/33] Ensure selected model after /model command is persisted
 before sending next prompt

---
 apps/cli/commands/ai/index.ts         | 17 ++++---
 apps/cli/commands/ai/tests/ai.test.ts | 73 +++++++++++++++++++--------
 2 files changed, 63 insertions(+), 27 deletions(-)

diff --git a/apps/cli/commands/ai/index.ts b/apps/cli/commands/ai/index.ts
index aff6c2fa78..1b38bb4a6f 100644
--- a/apps/cli/commands/ai/index.ts
+++ b/apps/cli/commands/ai/index.ts
@@ -122,6 +122,15 @@ export async function runCommand(
 		return persistQueue;
 	};
 
+	async function persistSessionContext(): Promise< void > {
+		await persist( ( recorder ) =>
+			recorder.recordSessionContext( {
+				provider: currentProvider,
+				model: currentModel,
+			} )
+		);
+	}
+
 	setProgressCallback( ( message ) => {
 		const timestamp = new Date().toISOString();
 		ui.setLoaderMessage( message );
@@ -261,12 +270,7 @@ export async function runCommand(
 			}]\n\n${ prompt }`;
 		}
 
-		await persist( ( recorder ) =>
-			recorder.recordSessionContext( {
-				provider: currentProvider,
-				model: currentModel,
-			} )
-		);
+		await persistSessionContext();
 
 		await persist( ( recorder ) =>
 			recorder.recordUserMessage( {
@@ -416,6 +420,7 @@ export async function runCommand(
 					currentModel = newModel[ 0 ];
 					ui.currentModel = currentModel;
 					ui.showInfo( `Switched to ${ AI_MODELS[ currentModel ] }` );
+					await persistSessionContext();
 				}
 				continue;
 			}
diff --git a/apps/cli/commands/ai/tests/ai.test.ts b/apps/cli/commands/ai/tests/ai.test.ts
index c157b1627d..f649ffff45 100644
--- a/apps/cli/commands/ai/tests/ai.test.ts
+++ b/apps/cli/commands/ai/tests/ai.test.ts
@@ -1,7 +1,7 @@
 import { __ } from '@wordpress/i18n';
 import { beforeEach, describe, expect, it, vi } from 'vitest';
 import yargs from 'yargs/yargs';
-import { startAiAgent } from 'cli/ai/agent';
+import { AI_MODELS, DEFAULT_MODEL, startAiAgent } from 'cli/ai/agent';
 import { resolveAiEnvironment, resolveInitialAiProvider } from 'cli/ai/auth';
 import { AiSessionRecorder } from 'cli/ai/sessions/recorder';
 import { deleteAiSession, listAiSessions, loadAiSession } from 'cli/ai/sessions/store';
@@ -12,19 +12,28 @@ import { registerCommand as registerAiSessionsResumeCommand } from 'cli/commands
 import { getAnthropicApiKey } from 'cli/lib/appdata';
 import { StudioArgv } from 'cli/types';
 
-const { reportErrorMock, waitForInputMock } = vi.hoisted( () => ( {
-	reportErrorMock: vi.fn(),
-	waitForInputMock: vi.fn(),
-} ) );
+const { askUserMock, recordSessionContextMock, reportErrorMock, waitForInputMock } = vi.hoisted(
+	() => ( {
+		askUserMock: vi.fn(),
+		recordSessionContextMock: vi.fn(),
+		reportErrorMock: vi.fn(),
+		waitForInputMock: vi.fn(),
+	} )
+);
 
-vi.mock( 'cli/lib/appdata', () => ( {
-	getAnthropicApiKey: vi.fn(),
-	getAuthToken: vi.fn().mockResolvedValue( {
-		displayName: 'Test User',
-		email: 'test@example.com',
-	} ),
-	saveAnthropicApiKey: vi.fn(),
-} ) );
+vi.mock( 'cli/lib/appdata', async () => {
+	const actual = await vi.importActual< typeof import('cli/lib/appdata') >( 'cli/lib/appdata' );
+
+	return {
+		...actual,
+		getAnthropicApiKey: vi.fn(),
+		getAuthToken: vi.fn().mockResolvedValue( {
+			displayName: 'Test User',
+			email: 'test@example.com',
+		} ),
+		saveAnthropicApiKey: vi.fn(),
+	};
+} );
 
 vi.mock( 'cli/ai/auth', () => ( {
 	getAvailableAiProviders: vi.fn().mockResolvedValue( [ 'anthropic-api-key', 'wpcom' ] ),
@@ -62,7 +71,8 @@ vi.mock( 'cli/logger', () => ( {
 	setProgressCallback: vi.fn(),
 } ) );
 
-vi.mock( 'cli/ai/agent', () => {
+vi.mock( 'cli/ai/agent', async () => {
+	const actual = await vi.importActual< typeof import('cli/ai/agent') >( 'cli/ai/agent' );
 	const emptyQuery = {
 		interrupt: vi.fn().mockResolvedValue( undefined ),
 		[ Symbol.asyncIterator ]() {
@@ -76,11 +86,7 @@ vi.mock( 'cli/ai/agent', () => {
 	};
 
 	return {
-		AI_MODELS: {
-			'claude-sonnet-4-6': 'Sonnet 4.6',
-			'claude-opus-4-6': 'Opus 4.6',
-		},
-		DEFAULT_MODEL: 'claude-sonnet-4-6',
+		...actual,
 		startAiAgent: vi.fn( () => emptyQuery ),
 	};
 } );
@@ -111,7 +117,7 @@ vi.mock( 'cli/ai/ui', () => ( {
 		}
 		showAgentQuestion() {}
 		async askUser() {
-			return {};
+			return askUserMock();
 		}
 		async waitForInput() {
 			return waitForInputMock();
@@ -127,7 +133,9 @@ vi.mock( 'cli/ai/sessions/recorder', () => {
 		static open = vi.fn().mockResolvedValue( new MockAiSessionRecorder() );
 		async recordSdkMessage() {}
 		async recordToolProgress() {}
-		async recordSessionContext() {}
+		async recordSessionContext( ...args: unknown[] ) {
+			return recordSessionContextMock( ...args );
+		}
 		async recordSiteSelected() {}
 		async recordUserMessage() {}
 		async recordAgentQuestion() {}
@@ -154,6 +162,7 @@ describe( 'CLI: studio ai sessions command', () => {
 	beforeEach( () => {
 		vi.clearAllMocks();
 		vi.mocked( getAnthropicApiKey ).mockResolvedValue( 'test-api-key' );
+		askUserMock.mockResolvedValue( {} );
 		waitForInputMock.mockResolvedValue( '/exit' );
 		vi.spyOn( process, 'exit' ).mockImplementation( () => undefined as never );
 	} );
@@ -198,6 +207,28 @@ describe( 'CLI: studio ai sessions command', () => {
 		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).create ).toHaveBeenCalledTimes( 1 );
 	} );
 
+	it( 'persists selected model before the first prompt is sent', async () => {
+		const alternateModel = ( Object.entries( AI_MODELS ) as [ string, string ][] ).find(
+			( [ modelId ] ) => modelId !== DEFAULT_MODEL
+		);
+		expect( alternateModel ).toBeDefined();
+		const [ selectedModelId, selectedModelLabel ] = alternateModel!;
+
+		waitForInputMock.mockResolvedValueOnce( '/model' ).mockResolvedValueOnce( '/exit' );
+		askUserMock.mockResolvedValueOnce( {
+			'Select a model': selectedModelLabel,
+		} );
+
+		await buildParser().parseAsync( [ 'ai' ] );
+
+		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).create ).toHaveBeenCalledTimes( 1 );
+		expect( recordSessionContextMock ).toHaveBeenCalledWith( {
+			provider: 'anthropic-api-key',
+			model: selectedModelId,
+		} );
+		expect( startAiAgent ).not.toHaveBeenCalled();
+	} );
+
 	it( 'disables session recording with --no-session-persistence', async () => {
 		await buildParser().parseAsync( [ 'ai', '--no-session-persistence' ] );
 

From 19ff5a6dbd9cd80643c2391b7789aa11084c0dad Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Thu, 19 Mar 2026 17:46:30 +0100
Subject: [PATCH 31/33] Use site.selected as the canonical source of truth for
 site selection

---
 apps/cli/ai/sessions/replay.ts              | 13 +------------
 apps/cli/commands/ai/tests/sessions.test.ts |  2 +-
 2 files changed, 2 insertions(+), 13 deletions(-)

diff --git a/apps/cli/ai/sessions/replay.ts b/apps/cli/ai/sessions/replay.ts
index e8a6751e5f..a52de7a65e 100644
--- a/apps/cli/ai/sessions/replay.ts
+++ b/apps/cli/ai/sessions/replay.ts
@@ -1,4 +1,3 @@
-import path from 'path';
 import { AiChatUI } from 'cli/ai/ui';
 import type { AiSessionEvent } from './types';
 
@@ -19,7 +18,7 @@ export function replaySessionHistory( ui: AiChatUI, events: AiSessionEvent[] ):
 						remote: event.remote === true,
 						url: typeof event.url === 'string' ? event.url : undefined,
 					},
-					{ announce: false, emitEvent: false }
+					{ announce: true, emitEvent: false }
 				);
 				continue;
 			}
@@ -34,16 +33,6 @@ export function replaySessionHistory( ui: AiChatUI, events: AiSessionEvent[] ):
 					ui.endAgentTurn();
 				}
 
-				if ( event.sitePath && ( ! ui.activeSite || ui.activeSite.path !== event.sitePath ) ) {
-					ui.setActiveSite(
-						{
-							name: path.basename( event.sitePath ),
-							path: event.sitePath,
-							running: false,
-						},
-						{ announce: false, emitEvent: false }
-					);
-				}
 				ui.beginAgentTurn();
 				isTurnOpen = true;
 				ui.addUserMessage( event.text );
diff --git a/apps/cli/commands/ai/tests/sessions.test.ts b/apps/cli/commands/ai/tests/sessions.test.ts
index 77cb02e69e..6d324b1dc9 100644
--- a/apps/cli/commands/ai/tests/sessions.test.ts
+++ b/apps/cli/commands/ai/tests/sessions.test.ts
@@ -515,7 +515,7 @@ describe( 'ai-sessions', () => {
 				remote: true,
 				url: 'https://my-remote-site.wordpress.com',
 			},
-			{ announce: false, emitEvent: false }
+			{ announce: true, emitEvent: false }
 		);
 	} );
 } );

From 3a955d1bb66290c79cf9a40a815a7a4ee5151f81 Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Fri, 20 Mar 2026 17:04:51 +0100
Subject: [PATCH 32/33] Remove unused cwd type

---
 apps/cli/ai/agent.ts | 1 -
 1 file changed, 1 deletion(-)

diff --git a/apps/cli/ai/agent.ts b/apps/cli/ai/agent.ts
index 4f971e61d8..f953cae088 100644
--- a/apps/cli/ai/agent.ts
+++ b/apps/cli/ai/agent.ts
@@ -16,7 +16,6 @@ export interface AiAgentConfig {
 	prompt: string;
 	env?: Record< string, string >;
 	model?: AiModelId;
-	cwd?: string;
 	maxTurns?: number;
 	resume?: string;
 	onAskUser?: ( questions: AskUserQuestion[] ) => Promise< Record< string, string > >;

From 08a1f9ecbb1b2020e180615071cfe73b47f35c7c Mon Sep 17 00:00:00 2001
From: Julien Verneaut <jverneaut@gmail.com>
Date: Fri, 20 Mar 2026 17:05:03 +0100
Subject: [PATCH 33/33] Persist session context on provider switch

---
 apps/cli/commands/ai/index.ts         |  1 +
 apps/cli/commands/ai/tests/ai.test.ts | 46 ++++++++++++++++++++++++++-
 2 files changed, 46 insertions(+), 1 deletion(-)

diff --git a/apps/cli/commands/ai/index.ts b/apps/cli/commands/ai/index.ts
index 1b38bb4a6f..8d4773f91b 100644
--- a/apps/cli/commands/ai/index.ts
+++ b/apps/cli/commands/ai/index.ts
@@ -173,6 +173,7 @@ export async function runCommand(
 		ui.currentProvider = currentProvider;
 		sessionId = undefined;
 		await saveSelectedAiProvider( currentProvider );
+		await persistSessionContext();
 		if ( announce ) {
 			ui.showInfo( `Switched to ${ AI_PROVIDERS[ currentProvider ] }` );
 		}
diff --git a/apps/cli/commands/ai/tests/ai.test.ts b/apps/cli/commands/ai/tests/ai.test.ts
index f649ffff45..a93dead792 100644
--- a/apps/cli/commands/ai/tests/ai.test.ts
+++ b/apps/cli/commands/ai/tests/ai.test.ts
@@ -2,7 +2,12 @@ import { __ } from '@wordpress/i18n';
 import { beforeEach, describe, expect, it, vi } from 'vitest';
 import yargs from 'yargs/yargs';
 import { AI_MODELS, DEFAULT_MODEL, startAiAgent } from 'cli/ai/agent';
-import { resolveAiEnvironment, resolveInitialAiProvider } from 'cli/ai/auth';
+import {
+	resolveAiEnvironment,
+	resolveInitialAiProvider,
+	resolveUnavailableAiProvider,
+} from 'cli/ai/auth';
+import { AI_PROVIDERS } from 'cli/ai/providers';
 import { AiSessionRecorder } from 'cli/ai/sessions/recorder';
 import { deleteAiSession, listAiSessions, loadAiSession } from 'cli/ai/sessions/store';
 import { registerCommand as registerAiCommand } from 'cli/commands/ai';
@@ -103,6 +108,7 @@ vi.mock( 'cli/ai/ui', () => ( {
 		showWelcome() {}
 		showInfo() {}
 		showError() {}
+		setStatusMessage() {}
 		prepareForReplay() {}
 		finishReplay() {}
 		beginAgentTurn() {}
@@ -158,6 +164,14 @@ vi.mock( 'cli/ai/sessions/replay', () => ( {
 	replaySessionHistory: vi.fn(),
 } ) );
 
+vi.mock( 'cli/commands/auth/login', () => ( {
+	runCommand: vi.fn().mockResolvedValue( undefined ),
+} ) );
+
+vi.mock( 'cli/commands/auth/logout', () => ( {
+	runCommand: vi.fn().mockResolvedValue( undefined ),
+} ) );
+
 describe( 'CLI: studio ai sessions command', () => {
 	beforeEach( () => {
 		vi.clearAllMocks();
@@ -229,6 +243,36 @@ describe( 'CLI: studio ai sessions command', () => {
 		expect( startAiAgent ).not.toHaveBeenCalled();
 	} );
 
+	it( 'persists selected provider before the first prompt is sent', async () => {
+		waitForInputMock.mockResolvedValueOnce( '/provider' ).mockResolvedValueOnce( '/exit' );
+		askUserMock.mockResolvedValueOnce( {
+			'Select an AI provider': AI_PROVIDERS.wpcom,
+		} );
+
+		await buildParser().parseAsync( [ 'ai' ] );
+
+		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).create ).toHaveBeenCalledTimes( 1 );
+		expect( recordSessionContextMock ).toHaveBeenCalledWith( {
+			provider: 'wpcom',
+			model: DEFAULT_MODEL,
+		} );
+		expect( startAiAgent ).not.toHaveBeenCalled();
+	} );
+
+	it( 'persists auto-switched provider after logout before any prompt is sent', async () => {
+		vi.mocked( resolveUnavailableAiProvider ).mockResolvedValueOnce( 'wpcom' );
+		waitForInputMock.mockResolvedValueOnce( '/logout' ).mockResolvedValueOnce( '/exit' );
+
+		await buildParser().parseAsync( [ 'ai' ] );
+
+		expect( ( AiSessionRecorder as typeof AiSessionRecorder ).create ).toHaveBeenCalledTimes( 1 );
+		expect( recordSessionContextMock ).toHaveBeenCalledWith( {
+			provider: 'wpcom',
+			model: DEFAULT_MODEL,
+		} );
+		expect( startAiAgent ).not.toHaveBeenCalled();
+	} );
+
 	it( 'disables session recording with --no-session-persistence', async () => {
 		await buildParser().parseAsync( [ 'ai', '--no-session-persistence' ] );