feat(desktop): opt-in clear history and continue from plan

products/desktop/packages/agent/src/adapters/claude/permissions/permission-handlers.ts

@@ -5,6 +5,7 @@ import type {
   ToolCallContent,
 } from "@agentclientprotocol/sdk";
 import type {
+  PermissionMode,
   PermissionRuleValue,
   PermissionUpdate,
 } from "@anthropic-ai/claude-agent-sdk";
@@ -39,6 +40,7 @@ import type { Session } from "../types";
 import {
   buildExitPlanModePermissionOptions,
   buildPermissionOptions,
+  CLEAR_AND_CONTINUE_OPTION_ID,
 } from "./permission-options";
 
 const SPEAK_TOOL_ID = qualifiedLocalToolName(SPEAK_TOOL_NAME);
@@ -284,32 +286,72 @@ async function requestPlanApproval(
   });
 }
 
+const PLAN_APPROVAL_MODE_OPTION_IDS = [
+  "auto",
+  "default",
+  "acceptEdits",
+  "bypassPermissions",
+] as const satisfies readonly PermissionMode[];
+
+function isPlanApprovalMode(value: string): value is PermissionMode {
+  return (PLAN_APPROVAL_MODE_OPTION_IDS as readonly string[]).includes(value);
+}
+
+function resolvePlanApprovalMode(
+  optionId: string,
+  response: RequestPermissionResponse,
+  previousMode?: string,
+): PermissionMode | null {
+  if (isPlanApprovalMode(optionId)) {
+    return optionId;
+  }
+
+  // Opt-in clear-and-continue: honor the ModeSelector choice when present,
+  // otherwise fall back to the mode the session was in before plan mode.
+  if (optionId === CLEAR_AND_CONTINUE_OPTION_ID) {
+    const answers = response._meta?.answers as
+      | Record<string, string>
+      | undefined;
+    const fromAnswers = answers?.executionMode;
+    if (typeof fromAnswers === "string" && isPlanApprovalMode(fromAnswers)) {
+      return fromAnswers;
+    }
+    if (previousMode && isPlanApprovalMode(previousMode)) {
+      return previousMode;
+    }
+    return "default";
+  }
+
+  return null;
+}
+
 async function applyPlanApproval(
   response: RequestPermissionResponse,
   context: ToolHandlerContext,
   updatedInput: Record<string, unknown>,
 ): Promise<ToolPermissionResult> {
-  if (
-    response.outcome?.outcome === "selected" &&
-    (response.outcome.optionId === "auto" ||
-      response.outcome.optionId === "default" ||
-      response.outcome.optionId === "acceptEdits" ||
-      response.outcome.optionId === "bypassPermissions")
-  ) {
-    await context.applySessionMode(response.outcome.optionId);
-    await context.updateConfigOption("mode", response.outcome.optionId);
+  if (response.outcome?.outcome === "selected") {
+    const mode = resolvePlanApprovalMode(
+      response.outcome.optionId,
+      response,
+      context.session.modeBeforePlan,
+    );
+    if (mode) {
+      await context.applySessionMode(mode);
+      await context.updateConfigOption("mode", mode);
 
-    return {
-      behavior: "allow",
-      updatedInput,
-      updatedPermissions: context.suggestions ?? [
-        {
-          type: "setMode",
-          mode: response.outcome.optionId,
-          destination: "localSettings",
-        },
-      ],
-    };
+      return {
+        behavior: "allow",
+        updatedInput,
+        updatedPermissions: context.suggestions ?? [
+          {
+            type: "setMode",
+            mode,
+            destination: "localSettings",
+          },
+        ],
+      };
+    }
   }
 
   const customInput = (response._meta as Record<string, unknown> | undefined)

products/desktop/packages/agent/src/adapters/claude/permissions/permission-options.test.ts

@@ -10,6 +10,20 @@ describe("buildExitPlanModePermissionOptions", () => {
     expect(options[options.length - 1].optionId).toBe("reject_with_feedback");
   });
 
+  it("includes an opt-in clear-and-continue option before reject", () => {
+    const options = buildExitPlanModePermissionOptions();
+    const clearIndex = options.findIndex(
+      (opt) => opt.optionId === "clearAndContinue",
+    );
+    expect(clearIndex).toBeGreaterThanOrEqual(0);
+    expect(options[clearIndex]).toMatchObject({
+      optionId: "clearAndContinue",
+      kind: "allow_once",
+      name: "Yes, clear history and continue from plan",
+    });
+    expect(options[clearIndex + 1]?.optionId).toBe("reject_with_feedback");
+  });
+
   it.each([
     {
       previousMode: "default",

products/desktop/packages/agent/src/adapters/claude/permissions/permission-options.ts

@@ -104,6 +104,9 @@ const CONTINUE_LABELS: Record<string, string> = {
   bypassPermissions: "Yes, continue bypassing all permissions",
 };
 
+/** Opt-in plan approval: clear planning context, then continue from the plan. */
+export const CLEAR_AND_CONTINUE_OPTION_ID = "clearAndContinue";
+
 export function buildExitPlanModePermissionOptions(
   previousMode?: string,
 ): PermissionOption[] {
@@ -151,6 +154,16 @@ export function buildExitPlanModePermissionOptions(
     }
   }
 
+  options.push({
+    kind: "allow_once",
+    name: "Yes, clear history and continue from plan",
+    optionId: CLEAR_AND_CONTINUE_OPTION_ID,
+    _meta: {
+      description:
+        "Discard planning conversation tokens and start implementation with a fresh context seeded by this plan",
+    },
+  });
+
   options.push({
     kind: "reject_once",
     name: "No, and tell the agent what to do differently",

products/desktop/packages/core/src/sessions/planContinuation.test.ts

@@ -0,0 +1,111 @@
+import type { PermissionRequest } from "@posthog/shared";
+import { describe, expect, it } from "vitest";
+import {
+  buildApprovedPlanContinuationPrompt,
+  CLEAR_AND_CONTINUE_OPTION_ID,
+  extractPlanMarkdownFromPermission,
+  isClearAndContinueOption,
+  isPlanApprovalAcceptOption,
+  isPlanApprovalPermission,
+  resolveClearAndContinueExecutionMode,
+  shouldContinueFromApprovedPlan,
+  toApprovedExecutionMode,
+} from "./planContinuation";
+
+function makePermission(
+  overrides: Partial<PermissionRequest> & {
+    toolCall?: PermissionRequest["toolCall"];
+  } = {},
+): PermissionRequest {
+  return {
+    taskRunId: "run-1",
+    receivedAt: 0,
+    options: [],
+    ...overrides,
+  } as PermissionRequest;
+}
+
+describe("planContinuation", () => {
+  it("detects plan approval permissions", () => {
+    expect(
+      isPlanApprovalPermission(
+        makePermission({ toolCall: { kind: "switch_mode" } as never }),
+      ),
+    ).toBe(true);
+    expect(
+      isPlanApprovalPermission(
+        makePermission({ toolCall: { kind: "execute" } as never }),
+      ),
+    ).toBe(false);
+  });
+
+  it("recognizes approve option ids", () => {
+    expect(isPlanApprovalAcceptOption("auto")).toBe(true);
+    expect(isPlanApprovalAcceptOption("reject_with_feedback")).toBe(false);
+    expect(isClearAndContinueOption(CLEAR_AND_CONTINUE_OPTION_ID)).toBe(true);
+    expect(isClearAndContinueOption("auto")).toBe(false);
+  });
+
+  it("only continues for the explicit clear-and-continue option", () => {
+    const permission = makePermission({
+      toolCall: { kind: "switch_mode" } as never,
+    });
+    expect(shouldContinueFromApprovedPlan(permission, "auto")).toBe(false);
+    expect(
+      shouldContinueFromApprovedPlan(permission, CLEAR_AND_CONTINUE_OPTION_ID),
+    ).toBe(true);
+    expect(
+      shouldContinueFromApprovedPlan(permission, "reject_with_feedback"),
+    ).toBe(false);
+  });
+
+  it("extracts trimmed plan markdown from rawInput", () => {
+    const permission = makePermission({
+      toolCall: {
+        kind: "switch_mode",
+        rawInput: { plan: "  ## Steps\n- one  " },
+      } as never,
+    });
+    expect(extractPlanMarkdownFromPermission(permission)).toBe(
+      "## Steps\n- one",
+    );
+    expect(
+      extractPlanMarkdownFromPermission(
+        makePermission({ toolCall: { kind: "switch_mode" } as never }),
+      ),
+    ).toBeNull();
+    // A non-string plan must not reach the continuation prompt.
+    expect(
+      extractPlanMarkdownFromPermission(
+        makePermission({
+          toolCall: { kind: "switch_mode", rawInput: { plan: 42 } } as never,
+        }),
+      ),
+    ).toBeNull();
+  });
+
+  it("maps approve option to execution mode", () => {
+    expect(toApprovedExecutionMode("auto")).toBe("auto");
+    expect(toApprovedExecutionMode("acceptEdits")).toBe("acceptEdits");
+  });
+
+  it("resolves clear-and-continue execution mode from answers", () => {
+    expect(
+      resolveClearAndContinueExecutionMode({ executionMode: "acceptEdits" }),
+    ).toBe("acceptEdits");
+    expect(resolveClearAndContinueExecutionMode({})).toBe("default");
+    expect(resolveClearAndContinueExecutionMode()).toBe("default");
+  });
+
+  it("builds a continuation prompt that embeds the plan", () => {
+    const blocks = buildApprovedPlanContinuationPrompt("## Fix\n- patch auth");
+    expect(blocks).toHaveLength(1);
+    expect(blocks[0]?.type).toBe("text");
+    const textBlock = blocks[0];
+    if (textBlock?.type !== "text") {
+      throw new Error("expected text block");
+    }
+    expect(textBlock.text).toContain("## Fix\n- patch auth");
+    expect(textBlock.text).toContain("execute this plan directly");
+  });
+});

products/desktop/packages/core/src/sessions/planContinuation.ts

@@ -0,0 +1,101 @@
+import type { ContentBlock } from "@agentclientprotocol/sdk";
+import type { ExecutionMode, PermissionRequest } from "@posthog/shared";
+import { z } from "zod";
+
+/** Option ids offered when approving ExitPlanMode (see buildExitPlanModePermissionOptions). */
+export const PLAN_APPROVAL_ACCEPT_OPTION_IDS = [
+  "auto",
+  "default",
+  "acceptEdits",
+  "bypassPermissions",
+] as const;
+
+export type PlanApprovalAcceptOptionId =
+  (typeof PLAN_APPROVAL_ACCEPT_OPTION_IDS)[number];
+
+/**
+ * Opt-in plan-approval option: clear planning context, then continue from the
+ * approved plan. Kept in sync with `CLEAR_AND_CONTINUE_OPTION_ID` in the Claude
+ * permission-options module (agent cannot import core).
+ */
+export const CLEAR_AND_CONTINUE_OPTION_ID = "clearAndContinue";
+
+/** Answers key used by the plan UI to carry the ModeSelector choice. */
+export const CLEAR_AND_CONTINUE_EXECUTION_MODE_KEY = "executionMode";
+
+/**
+ * The adapter intercepts this before the SDK conversion and swaps in a fresh
+ * SDK session, so it is how core asks for a clear.
+ */
+export const CLEAR_CONVERSATION_COMMAND = "/clear";
+
+export function isPlanApprovalPermission(
+  permission: PermissionRequest,
+): boolean {
+  return permission.toolCall?.kind === "switch_mode";
+}
+
+export function isPlanApprovalAcceptOption(
+  optionId: string,
+): optionId is PlanApprovalAcceptOptionId {
+  return (PLAN_APPROVAL_ACCEPT_OPTION_IDS as readonly string[]).includes(
+    optionId,
+  );
+}
+
+export function isClearAndContinueOption(optionId: string): boolean {
+  return optionId === CLEAR_AND_CONTINUE_OPTION_ID;
+}
+
+/**
+ * Only the explicit "clear history and continue from plan" option triggers a
+ * fresh implementation session — normal approve keeps the planning context.
+ */
+export function shouldContinueFromApprovedPlan(
+  permission: PermissionRequest,
+  optionId: string,
+): boolean {
+  return (
+    isPlanApprovalPermission(permission) && isClearAndContinueOption(optionId)
+  );
+}
+
+/** ExitPlanMode carries the approved plan as markdown on its tool input. */
+const planToolInputSchema = z.object({ plan: z.string() });
+
+export function extractPlanMarkdownFromPermission(
+  permission: PermissionRequest,
+): string | null {
+  const parsed = planToolInputSchema.safeParse(permission.toolCall?.rawInput);
+  if (!parsed.success) return null;
+  const trimmed = parsed.data.plan.trim();
+  return trimmed.length > 0 ? trimmed : null;
+}
+
+export function toApprovedExecutionMode(
+  optionId: PlanApprovalAcceptOptionId,
+): ExecutionMode {
+  return optionId;
+}
+
+export function resolveClearAndContinueExecutionMode(
+  answers?: Record<string, string>,
+): ExecutionMode {
+  const mode = answers?.[CLEAR_AND_CONTINUE_EXECUTION_MODE_KEY];
+  if (mode && isPlanApprovalAcceptOption(mode)) {
+    return toApprovedExecutionMode(mode);
+  }
+  return "default";
+}
+
+export function buildApprovedPlanContinuationPrompt(
+  planMarkdown: string,
+): ContentBlock[] {
+  const text = [
+    "The user approved the implementation plan below. Planning is complete — execute this plan directly.",
+    "Do not re-enter plan mode unless the user asks for a significant change in direction.",
+    "",
+    planMarkdown,
+  ].join("\n");
+  return [{ type: "text", text }];
+}