diff --git a/apps/cli/ai/slash-commands.ts b/apps/cli/ai/slash-commands.ts
index 76eabb5e54..0f2eb3b4c7 100644
--- a/apps/cli/ai/slash-commands.ts
+++ b/apps/cli/ai/slash-commands.ts
@@ -10,13 +10,73 @@ export const AI_CHAT_LOGOUT_COMMAND = '/logout';
 export const AI_CHAT_MODEL_COMMAND = '/model';
 export const AI_CHAT_PROVIDER_COMMAND = '/provider';
 export const AI_CHAT_EXIT_COMMAND = '/exit';
+export const AI_CHAT_CLASSIC_TO_BLOCKS_COMMAND = '/classic-to-blocks';
 
 export const AI_CHAT_SLASH_COMMANDS: SlashCommandDef[] = [
 	{ name: 'browser', description: 'Open the active site in the browser' },
 	{ name: 'api-key', description: 'Set or update the Anthropic API key' },
+	{ name: 'classic-to-blocks', description: 'Convert the active classic theme to a block theme' },
 	{ name: 'login', description: 'Log in to WordPress.com' },
 	{ name: 'logout', description: 'Log out of WordPress.com' },
 	{ name: 'model', description: 'Switch the AI model' },
 	{ name: 'provider', description: 'Switch the AI provider' },
 	{ name: 'exit', description: 'Exit the chat' },
 ];
+
+export const CLASSIC_TO_BLOCKS_PROMPT = `Convert the active site's current classic PHP theme into a fully functional WordPress block theme. Follow these steps precisely:
+
+## Step 1: Capture the current design
+
+Before making ANY changes, capture visual reference of the classic theme:
+1. Use site_info to get the site URL.
+2. Use take_screenshot on the site's homepage (desktop and mobile).
+3. Take screenshots of other key pages if they exist (check with wp_cli: \`post list --post_type=page --post_status=publish --fields=ID,post_title,post_name\`).
+4. Save these screenshots mentally as the "target" — the block theme MUST look identical.
+
+## Step 2: Analyze the classic theme
+
+Read and understand the entire classic theme structure:
+1. List all theme files with Glob (*.php, *.css, *.js in the theme directory).
+2. Read every PHP template file: index.php, header.php, footer.php, sidebar.php, single.php, page.php, archive.php, functions.php, and any custom templates.
+3. Read style.css fully — every CSS rule matters.
+4. Read any JS files.
+5. Identify: the header structure, navigation menus, footer structure, sidebars/widgets, custom post type templates, template hierarchy usage, enqueued styles/scripts, custom functions, theme supports, and customizer settings.
+
+## Step 3: Create the block theme
+
+Create a NEW block theme (do not modify the classic theme in place). Name it with "-blocks" appended (e.g., "flavor-blocks" for "flavor"):
+
+### Required files:
+- **style.css**: Theme header + ALL the original CSS rules, adapted for block markup. Selectors may need updating since block themes use different markup (e.g., \`.wp-block-navigation\` instead of custom menu markup).
+- **theme.json**: Define colors, typography, spacing, and layout settings matching the classic theme's design. Use the original fonts, colors, and sizes.
+- **functions.php**: Enqueue styles, register block patterns, add theme supports. Keep any custom functionality from the original.
+- **templates/index.html**: Main template using blocks.
+- **templates/page.html**: Page template.
+- **templates/single.html**: Single post template.
+- **templates/archive.html**: Archive/category template.
+- **templates/404.html**: 404 page.
+- **templates/front-page.html**: If the original has a custom front page.
+- **parts/header.html**: Header template part — must match the original header exactly (logo, navigation, any top bars).
+- **parts/footer.html**: Footer template part — must match the original footer exactly.
+
+### Conversion rules:
+- PHP template tags → block equivalents: \`the_title()\` → \`core/post-title\`, \`the_content()\` → \`core/post-content\`, \`the_excerpt()\` → \`core/post-excerpt\`, \`wp_nav_menu()\` → \`core/navigation\`, \`get_header()\`/\`get_footer()\` → template parts, \`the_post_thumbnail()\` → \`core/post-featured-image\`, \`get_search_form()\` → \`core/search\`, \`dynamic_sidebar()\` → relevant blocks, loops → \`core/query\` + \`core/post-template\`.
+- Custom PHP logic → block patterns or custom blocks where necessary.
+- Preserve ALL visual styling — every color, font, spacing, border, shadow, hover effect.
+- Preserve responsive behavior.
+
+## Step 4: Activate and validate
+
+1. Activate the new block theme: \`wp_cli theme activate <new-theme-slug>\`.
+2. Use take_screenshot on every page you captured in Step 1.
+3. Compare side by side with the original screenshots. Fix ANY visual differences:
+   - Header layout and navigation
+   - Typography (fonts, sizes, weights, line heights)
+   - Colors (backgrounds, text, links, accents)
+   - Spacing (margins, padding)
+   - Footer layout
+   - Responsive behavior (check mobile too)
+4. Run validate_blocks on all template files to ensure block validity.
+5. Iterate until the block theme is visually indistinguishable from the classic theme.
+
+IMPORTANT: The goal is VISUAL PARITY. The block theme must look exactly like the classic theme. Do not "improve" or "modernize" the design — reproduce it faithfully.`;
diff --git a/apps/cli/commands/ai.ts b/apps/cli/commands/ai.ts
index e3590558d0..a4131a70c4 100644
--- a/apps/cli/commands/ai.ts
+++ b/apps/cli/commands/ai.ts
@@ -13,11 +13,13 @@ import { AI_PROVIDERS, type AiProviderId } from 'cli/ai/providers';
 import {
 	AI_CHAT_API_KEY_COMMAND,
 	AI_CHAT_BROWSER_COMMAND,
+	AI_CHAT_CLASSIC_TO_BLOCKS_COMMAND,
 	AI_CHAT_EXIT_COMMAND,
 	AI_CHAT_LOGIN_COMMAND,
 	AI_CHAT_LOGOUT_COMMAND,
 	AI_CHAT_MODEL_COMMAND,
 	AI_CHAT_PROVIDER_COMMAND,
+	CLASSIC_TO_BLOCKS_PROMPT,
 } from 'cli/ai/slash-commands';
 import { AiChatUI } from 'cli/ai/ui';
 import { runCommand as runLoginCommand } from 'cli/commands/auth/login';
@@ -211,6 +213,16 @@ export async function runCommand(): Promise< void > {
 				continue;
 			}
 
+			if ( trimmedPrompt === AI_CHAT_CLASSIC_TO_BLOCKS_COMMAND ) {
+				if ( ! ui.activeSite ) {
+					ui.showInfo( 'No site selected. Use ↓ to select a site with a classic theme first.' );
+					continue;
+				}
+				ui.addUserMessage( '/classic-to-blocks' );
+				await runAgentTurn( CLASSIC_TO_BLOCKS_PROMPT );
+				continue;
+			}
+
 			if ( trimmedPrompt === AI_CHAT_LOGIN_COMMAND ) {
 				ui.stop();
 				await runLoginCommand();