complete

packages/cli/src/test-utils/render.tsx

@@ -591,6 +591,7 @@ const mockUIActions: UIActions = {
   setConstrainHeight: vi.fn(),
   onEscapePromptChange: vi.fn(),
   refreshStatic: vi.fn(),
+  handleClearPlanContext: vi.fn(),
   handleFinalSubmit: vi.fn(),
   handleClearScreen: vi.fn(),
   handleProQuotaChoice: vi.fn(),

packages/cli/src/ui/AppContainer.tsx

@@ -50,7 +50,7 @@ import {
   type GeminiUserTier,
   type UserFeedbackPayload,
   type AgentDefinition,
-  type ApprovalMode,
+  ApprovalMode,
   IdeClient,
   ideContextStore,
   getErrorMessage,
@@ -398,6 +398,20 @@ export const AppContainer = (props: AppContainerProps) => {
   );
 
   const [isConfigInitialized, setConfigInitialized] = useState(false);
+  const [planModeUIHistoryStartIndex, setPlanModeUIHistoryStartIndex] =
+    useState<number | null>(null);
+
+  useEffect(() => {
+    const handleApprovalModeChanged = ({ mode }: { mode: ApprovalMode }) => {
+      if (mode === ApprovalMode.PLAN) {
+        setPlanModeUIHistoryStartIndex(historyManager.history.length);
+      }
+    };
+    coreEvents.on(CoreEvent.ApprovalModeChanged, handleApprovalModeChanged);
+    return () => {
+      coreEvents.off(CoreEvent.ApprovalModeChanged, handleApprovalModeChanged);
+    };
+  }, [historyManager.history.length]);
 
   const logger = useLogger(config.storage);
   const { inputHistory, addInput, initializeFromLogger } =
@@ -1346,6 +1360,17 @@ Logging in with Google... Restarting Gemini CLI to continue.
     triggerExpandHint,
   ]);
 
+  const handleClearPlanContext = useCallback(() => {
+    if (planModeUIHistoryStartIndex !== null) {
+      const newHistory = historyManager.history.slice(
+        0,
+        planModeUIHistoryStartIndex,
+      );
+      historyManager.loadHistory(newHistory);
+      refreshStatic();
+    }
+  }, [planModeUIHistoryStartIndex, historyManager, refreshStatic]);
+
   const { handleInput: vimHandleInput } = useVim(buffer, handleFinalSubmit);
 
   /**
@@ -2456,6 +2481,7 @@ Logging in with Google... Restarting Gemini CLI to continue.
       setConstrainHeight,
       onEscapePromptChange: handleEscapePromptChange,
       refreshStatic,
+      handleClearPlanContext,
       handleFinalSubmit,
       handleClearScreen,
       handleProQuotaChoice,
@@ -2548,6 +2574,7 @@ Logging in with Google... Restarting Gemini CLI to continue.
       setConstrainHeight,
       handleEscapePromptChange,
       refreshStatic,
+      handleClearPlanContext,
       handleFinalSubmit,
       handleClearScreen,
       handleProQuotaChoice,

packages/cli/src/ui/components/ExitPlanModeDialog.test.tsx

@@ -207,7 +207,7 @@ Implement a comprehensive authentication system with multiple providers.
         writeKey(stdin, '\r');
 
         await waitFor(() => {
-          expect(onApprove).toHaveBeenCalledWith(ApprovalMode.AUTO_EDIT);
+          expect(onApprove).toHaveBeenCalledWith(ApprovalMode.AUTO_EDIT, false);
         });
       });
 
@@ -222,11 +222,12 @@ Implement a comprehensive authentication system with multiple providers.
           expect(lastFrame()).toContain('Add user authentication');
         });
 
+        writeKey(stdin, '\x1b[B'); // Down arrow
         writeKey(stdin, '\x1b[B'); // Down arrow
         writeKey(stdin, '\r');
 
         await waitFor(() => {
-          expect(onApprove).toHaveBeenCalledWith(ApprovalMode.DEFAULT);
+          expect(onApprove).toHaveBeenCalledWith(ApprovalMode.DEFAULT, false);
         });
       });
 
@@ -349,11 +350,11 @@ Implement a comprehensive authentication system with multiple providers.
           expect(lastFrame()).toContain('Add user authentication');
         });
 
-        // Press '2' to select second option directly
-        writeKey(stdin, '2');
+        // Press '3' to select third option directly
+        writeKey(stdin, '3');
 
         await waitFor(() => {
-          expect(onApprove).toHaveBeenCalledWith(ApprovalMode.DEFAULT);
+          expect(onApprove).toHaveBeenCalledWith(ApprovalMode.DEFAULT, false);
         });
       });
 
@@ -371,6 +372,8 @@ Implement a comprehensive authentication system with multiple providers.
         // Navigate to feedback option and start typing
         writeKey(stdin, '\x1b[B'); // Down arrow
         writeKey(stdin, '\x1b[B'); // Down arrow
+        writeKey(stdin, '\x1b[B'); // Down arrow
+        writeKey(stdin, '\x1b[B'); // Down arrow
         writeKey(stdin, '\r'); // Select to focus input
 
         // Type some feedback
@@ -493,7 +496,9 @@ Implement a comprehensive authentication system with multiple providers.
           expect(lastFrame()).toContain('Add user authentication');
         });
 
-        // Navigate to feedback option
+        // Focus feedback option
+        writeKey(stdin, '\x1b[B'); // Down arrow
+        writeKey(stdin, '\x1b[B'); // Down arrow
         writeKey(stdin, '\x1b[B'); // Down arrow
         writeKey(stdin, '\x1b[B'); // Down arrow
 
@@ -523,6 +528,8 @@ Implement a comprehensive authentication system with multiple providers.
         // Navigate to feedback option and start typing
         writeKey(stdin, '\x1b[B'); // Down arrow
         writeKey(stdin, '\x1b[B'); // Down arrow
+        writeKey(stdin, '\x1b[B'); // Down arrow
+        writeKey(stdin, '\x1b[B'); // Down arrow
 
         // Type some feedback
         for (const char of 'test') {
@@ -531,12 +538,13 @@ Implement a comprehensive authentication system with multiple providers.
 
         // Now use up arrow to navigate back to a different option
         writeKey(stdin, '\x1b[A'); // Up arrow
+        writeKey(stdin, '\x1b[A'); // Up arrow
 
-        // Press Enter to select the second option (manually accept edits)
+        // Press Enter to select the manually accept edits option
         writeKey(stdin, '\r');
 
         await waitFor(() => {
-          expect(onApprove).toHaveBeenCalledWith(ApprovalMode.DEFAULT);
+          expect(onApprove).toHaveBeenCalledWith(ApprovalMode.DEFAULT, false);
         });
         expect(onFeedback).not.toHaveBeenCalled();
       });

packages/cli/src/ui/components/ExitPlanModeDialog.tsx

@@ -27,7 +27,7 @@ import { formatCommand } from '../utils/keybindingUtils.js';
 
 export interface ExitPlanModeDialogProps {
   planPath: string;
-  onApprove: (approvalMode: ApprovalMode) => void;
+  onApprove: (approvalMode: ApprovalMode, clearConversation?: boolean) => void;
   onFeedback: (feedback: string) => void;
   onCancel: () => void;
   getPreferredEditor: () => EditorType | undefined;
@@ -50,7 +50,9 @@ interface PlanContentState {
 
 enum ApprovalOption {
   Auto = 'Yes, automatically accept edits',
+  AutoClear = 'Yes, automatically accept edits & clear conversation',
   Manual = 'Yes, manually accept edits',
+  ManualClear = 'Yes, manually accept edits & clear conversation',
 }
 
 /**
@@ -239,11 +241,21 @@ export const ExitPlanModeDialog: React.FC<ExitPlanModeDialogProps> = ({
                 description:
                   'Approves plan and allows tools to run automatically',
               },
+              {
+                label: ApprovalOption.AutoClear,
+                description:
+                  'Approves plan, runs automatically, and clears prior conversation context',
+              },
               {
                 label: ApprovalOption.Manual,
                 description:
                   'Approves plan but requires confirmation for each tool',
               },
+              {
+                label: ApprovalOption.ManualClear,
+                description:
+                  'Approves plan, requires confirmation, and clears prior conversation context',
+              },
             ],
             placeholder: 'Type your feedback...',
             multiSelect: false,
@@ -251,10 +263,19 @@ export const ExitPlanModeDialog: React.FC<ExitPlanModeDialogProps> = ({
         ]}
         onSubmit={(answers) => {
           const answer = answers['0'];
-          if (answer === ApprovalOption.Auto) {
-            onApprove(ApprovalMode.AUTO_EDIT);
-          } else if (answer === ApprovalOption.Manual) {
-            onApprove(ApprovalMode.DEFAULT);
+          const clearConversation =
+            answer === ApprovalOption.AutoClear ||
+            answer === ApprovalOption.ManualClear;
+          if (
+            answer === ApprovalOption.Auto ||
+            answer === ApprovalOption.AutoClear
+          ) {
+            onApprove(ApprovalMode.AUTO_EDIT, clearConversation);
+          } else if (
+            answer === ApprovalOption.Manual ||
+            answer === ApprovalOption.ManualClear
+          ) {
+            onApprove(ApprovalMode.DEFAULT, clearConversation);
           } else if (answer) {
             onFeedback(answer);
           }

packages/cli/src/ui/components/__snapshots__/ExitPlanModeDialog.test.tsx.snap

@@ -17,43 +17,19 @@ Files to Modify
  - src/index.ts - Add auth middleware
  - src/config.ts - Add auth configuration options
 
+▲
   1.  Yes, automatically accept edits
       Approves plan and allows tools to run automatically
-● 2.  Yes, manually accept edits                                                
-      Approves plan but requires confirmation for each tool                     
-  3.  Type your feedback...
+● 2.  Yes, automatically accept edits & clear conversation                      
+      Approves plan, runs automatically, and clears prior conversation context  
+  3.  Yes, manually accept edits
+      Approves plan but requires confirmation for each tool
+▼
 
 Enter to select · ↑/↓ to navigate · Ctrl+X to edit plan · Esc to cancel
 "
 `;
 
-exports[`ExitPlanModeDialog > useAlternateBuffer: false > bubbles up Ctrl+C when feedback is empty while editing 2`] = `
-"Overview
-
-Add user authentication to the CLI application.
-
-Implementation Steps
-
- 1. Create src/auth/AuthService.ts with login/logout methods
- 2. Add session storage in src/storage/SessionStore.ts
- 3. Update src/commands/index.ts to check auth status
- 4. Add tests in src/auth/__tests__/
-
-Files to Modify
-
- - src/index.ts - Add auth middleware
- - src/config.ts - Add auth configuration options
-
-  1.  Yes, automatically accept edits
-      Approves plan and allows tools to run automatically
-  2.  Yes, manually accept edits
-      Approves plan but requires confirmation for each tool
-● 3.  Type your feedback...
-
-Enter to submit · Ctrl+X to edit plan · Esc to cancel
-"
-`;
-
 exports[`ExitPlanModeDialog > useAlternateBuffer: false > calls onFeedback when feedback is typed and submitted 1`] = `
 "Overview
 
@@ -71,43 +47,19 @@ Files to Modify
  - src/index.ts - Add auth middleware
  - src/config.ts - Add auth configuration options
 
+▲
 ● 1.  Yes, automatically accept edits                                           
       Approves plan and allows tools to run automatically                       
-  2.  Yes, manually accept edits
+  2.  Yes, automatically accept edits & clear conversation
+      Approves plan, runs automatically, and clears prior conversation context
+  3.  Yes, manually accept edits
       Approves plan but requires confirmation for each tool
-  3.  Type your feedback...
+▼
 
 Enter to select · ↑/↓ to navigate · Ctrl+X to edit plan · Esc to cancel
 "
 `;
 
-exports[`ExitPlanModeDialog > useAlternateBuffer: false > calls onFeedback when feedback is typed and submitted 2`] = `
-"Overview
-
-Add user authentication to the CLI application.
-
-Implementation Steps
-
- 1. Create src/auth/AuthService.ts with login/logout methods
- 2. Add session storage in src/storage/SessionStore.ts
- 3. Update src/commands/index.ts to check auth status
- 4. Add tests in src/auth/__tests__/
-
-Files to Modify
-
- - src/index.ts - Add auth middleware
- - src/config.ts - Add auth configuration options
-
-  1.  Yes, automatically accept edits
-      Approves plan and allows tools to run automatically
-  2.  Yes, manually accept edits
-      Approves plan but requires confirmation for each tool
-● 3.  Add tests
-
-Enter to submit · Ctrl+X to edit plan · Esc to cancel
-"
-`;
-
 exports[`ExitPlanModeDialog > useAlternateBuffer: false > displays error state when file read fails 1`] = `
 " Error reading plan: File not found
 "
@@ -130,11 +82,14 @@ Implementation Steps
  8. Add multi-factor authentication in src/auth/MFAService.ts
 ... last 22 lines hidden (Ctrl+O to show) ...
 
+▲
 ● 1.  Yes, automatically accept edits                                           
       Approves plan and allows tools to run automatically                       
-  2.  Yes, manually accept edits
+  2.  Yes, automatically accept edits & clear conversation
+      Approves plan, runs automatically, and clears prior conversation context
+  3.  Yes, manually accept edits
       Approves plan but requires confirmation for each tool
-  3.  Type your feedback...
+▼
 
 Enter to select · ↑/↓ to navigate · Ctrl+X to edit plan · Esc to cancel
 "
@@ -157,11 +112,14 @@ Files to Modify
  - src/index.ts - Add auth middleware
  - src/config.ts - Add auth configuration options
 
+▲
 ● 1.  Yes, automatically accept edits                                           
       Approves plan and allows tools to run automatically                       
-  2.  Yes, manually accept edits
+  2.  Yes, automatically accept edits & clear conversation
+      Approves plan, runs automatically, and clears prior conversation context
+  3.  Yes, manually accept edits
       Approves plan but requires confirmation for each tool
-  3.  Type your feedback...
+▼
 
 Enter to select · ↑/↓ to navigate · Ctrl+X to edit plan · Esc to cancel
 "
@@ -186,41 +144,19 @@ Files to Modify
 
   1.  Yes, automatically accept edits
       Approves plan and allows tools to run automatically
-● 2.  Yes, manually accept edits                                                
-      Approves plan but requires confirmation for each tool                     
-  3.  Type your feedback...
+● 2.  Yes, automatically accept edits & clear conversation                      
+      Approves plan, runs automatically, and clears prior conversation context  
+  3.  Yes, manually accept edits
+      Approves plan but requires confirmation for each tool
+  4.  Yes, manually accept edits & clear conversation
+      Approves plan, requires confirmation, and clears prior conversation
+     context
+  5.  Type your feedback...
 
 Enter to select · ↑/↓ to navigate · Ctrl+X to edit plan · Esc to cancel
 "
 `;
 
-exports[`ExitPlanModeDialog > useAlternateBuffer: true > bubbles up Ctrl+C when feedback is empty while editing 2`] = `
-"Overview
-
-Add user authentication to the CLI application.
-
-Implementation Steps
-
- 1. Create src/auth/AuthService.ts with login/logout methods
- 2. Add session storage in src/storage/SessionStore.ts
- 3. Update src/commands/index.ts to check auth status
- 4. Add tests in src/auth/__tests__/
-
-Files to Modify
-
- - src/index.ts - Add auth middleware
- - src/config.ts - Add auth configuration options
-
-  1.  Yes, automatically accept edits
-      Approves plan and allows tools to run automatically
-  2.  Yes, manually accept edits
-      Approves plan but requires confirmation for each tool
-● 3.  Type your feedback...
-
-Enter to submit · Ctrl+X to edit plan · Esc to cancel
-"
-`;
-
 exports[`ExitPlanModeDialog > useAlternateBuffer: true > calls onFeedback when feedback is typed and submitted 1`] = `
 "Overview
 
@@ -240,41 +176,19 @@ Files to Modify
 
 ● 1.  Yes, automatically accept edits                                           
       Approves plan and allows tools to run automatically                       
-  2.  Yes, manually accept edits
+  2.  Yes, automatically accept edits & clear conversation
+      Approves plan, runs automatically, and clears prior conversation context
+  3.  Yes, manually accept edits
       Approves plan but requires confirmation for each tool
-  3.  Type your feedback...
+  4.  Yes, manually accept edits & clear conversation
+      Approves plan, requires confirmation, and clears prior conversation
+     context
+  5.  Type your feedback...
 
 Enter to select · ↑/↓ to navigate · Ctrl+X to edit plan · Esc to cancel
 "
 `;
 
-exports[`ExitPlanModeDialog > useAlternateBuffer: true > calls onFeedback when feedback is typed and submitted 2`] = `
-"Overview
-
-Add user authentication to the CLI application.
-
-Implementation Steps
-
- 1. Create src/auth/AuthService.ts with login/logout methods
- 2. Add session storage in src/storage/SessionStore.ts
- 3. Update src/commands/index.ts to check auth status
- 4. Add tests in src/auth/__tests__/
-
-Files to Modify
-
- - src/index.ts - Add auth middleware
- - src/config.ts - Add auth configuration options
-
-  1.  Yes, automatically accept edits
-      Approves plan and allows tools to run automatically
-  2.  Yes, manually accept edits
-      Approves plan but requires confirmation for each tool
-● 3.  Add tests
-
-Enter to submit · Ctrl+X to edit plan · Esc to cancel
-"
-`;
-
 exports[`ExitPlanModeDialog > useAlternateBuffer: true > displays error state when file read fails 1`] = `
 " Error reading plan: File not found
 "
@@ -320,9 +234,14 @@ Testing Strategy
 
 ● 1.  Yes, automatically accept edits                                           
       Approves plan and allows tools to run automatically                       
-  2.  Yes, manually accept edits
+  2.  Yes, automatically accept edits & clear conversation
+      Approves plan, runs automatically, and clears prior conversation context
+  3.  Yes, manually accept edits
       Approves plan but requires confirmation for each tool
-  3.  Type your feedback...
+  4.  Yes, manually accept edits & clear conversation
+      Approves plan, requires confirmation, and clears prior conversation
+     context
+  5.  Type your feedback...
 
 Enter to select · ↑/↓ to navigate · Ctrl+X to edit plan · Esc to cancel
 "
@@ -347,9 +266,14 @@ Files to Modify
 
 ● 1.  Yes, automatically accept edits                                           
       Approves plan and allows tools to run automatically                       
-  2.  Yes, manually accept edits
+  2.  Yes, automatically accept edits & clear conversation
+      Approves plan, runs automatically, and clears prior conversation context
+  3.  Yes, manually accept edits
       Approves plan but requires confirmation for each tool
-  3.  Type your feedback...
+  4.  Yes, manually accept edits & clear conversation
+      Approves plan, requires confirmation, and clears prior conversation
+     context
+  5.  Type your feedback...
 
 Enter to select · ↑/↓ to navigate · Ctrl+X to edit plan · Esc to cancel
 "

packages/cli/src/ui/components/messages/ToolConfirmationMessage.tsx

@@ -29,6 +29,7 @@ import {
 import { useKeypress } from '../../hooks/useKeypress.js';
 import { theme } from '../../semantic-colors.js';
 import { useSettings } from '../../contexts/SettingsContext.js';
+import { useUIActions } from '../../contexts/UIActionsContext.js';
 import { keyMatchers, Command } from '../../keyMatchers.js';
 import { formatCommand } from '../../utils/keybindingUtils.js';
 import {
@@ -68,6 +69,7 @@ export const ToolConfirmationMessage: React.FC<
   terminalWidth,
 }) => {
   const { confirm, isDiffingEnabled } = useToolActions();
+  const { handleClearPlanContext } = useUIActions();
   const [mcpDetailsExpansionState, setMcpDetailsExpansionState] = useState<{
     callId: string;
     expanded: boolean;
@@ -428,10 +430,14 @@ export const ToolConfirmationMessage: React.FC<
         <ExitPlanModeDialog
           planPath={confirmationDetails.planPath}
           getPreferredEditor={getPreferredEditor}
-          onApprove={(approvalMode) => {
+          onApprove={(approvalMode, clearConversation) => {
+            if (clearConversation) {
+              handleClearPlanContext();
+            }
             handleConfirm(ToolConfirmationOutcome.ProceedOnce, {
               approved: true,
               approvalMode,
+              clearConversation,
             });
           }}
           onFeedback={(feedback) => {
@@ -623,17 +629,18 @@ export const ToolConfirmationMessage: React.FC<
 
     return { question, bodyContent, options, securityWarnings };
   }, [
-    confirmationDetails,
     getOptions,
-    availableBodyContentHeight,
-    terminalWidth,
-    handleConfirm,
     deceptiveUrlWarningText,
-    isMcpToolDetailsExpanded,
-    hasMcpToolDetails,
-    mcpToolDetailsText,
-    expandDetailsHintKey,
+    confirmationDetails,
+    terminalWidth,
+    availableBodyContentHeight,
+    handleConfirm,
     getPreferredEditor,
+    handleClearPlanContext,
+    hasMcpToolDetails,
+    isMcpToolDetailsExpanded,
+    expandDetailsHintKey,
+    mcpToolDetailsText,
   ]);
 
   const bodyOverflowDirection: 'top' | 'bottom' =

packages/cli/src/ui/contexts/UIActionsContext.tsx

@@ -57,6 +57,7 @@ export interface UIActions {
   setConstrainHeight: (value: boolean) => void;
   onEscapePromptChange: (show: boolean) => void;
   refreshStatic: () => void;
+  handleClearPlanContext: () => void;
   handleFinalSubmit: (value: string) => Promise<void>;
   handleClearScreen: () => void;
   handleProQuotaChoice: (

packages/core/src/config/config.ts

@@ -1960,6 +1960,12 @@ export class Config implements McpContext {
     this.geminiMdFilePaths = paths;
   }
 
+  private planModeHistoryStartIndex = 0;
+
+  getPlanModeHistoryStartIndex(): number {
+    return this.planModeHistoryStartIndex;
+  }
+
   getApprovalMode(): ApprovalMode {
     return this.policyEngine.getApprovalMode();
   }
@@ -2017,6 +2023,14 @@ export class Config implements McpContext {
 
     this.policyEngine.setApprovalMode(mode);
 
+    if (mode === ApprovalMode.PLAN && currentMode !== ApprovalMode.PLAN) {
+      this.planModeHistoryStartIndex = this.geminiClient?.isInitialized()
+        ? this.geminiClient.getHistory().length
+        : 0;
+    }
+
+    coreEvents.emitApprovalModeChanged(mode);
+
     const isPlanModeTransition =
       currentMode !== mode &&
       (currentMode === ApprovalMode.PLAN || mode === ApprovalMode.PLAN);

packages/core/src/tools/exit-plan-mode.test.ts

@@ -9,6 +9,7 @@ import { ExitPlanModeTool, ExitPlanModeInvocation } from './exit-plan-mode.js';
 import { createMockMessageBus } from '../test-utils/mock-message-bus.js';
 import path from 'node:path';
 import type { Config } from '../config/config.js';
+import type { GeminiClient } from '../core/client.js';
 import type { MessageBus } from '../confirmation-bus/message-bus.js';
 import { ToolConfirmationOutcome } from './tools.js';
 import { ApprovalMode } from '../policy/types.js';
@@ -44,6 +45,8 @@ describe('ExitPlanModeTool', () => {
       getTargetDir: vi.fn().mockReturnValue(tempRootDir),
       setApprovalMode: vi.fn(),
       setApprovedPlanPath: vi.fn(),
+      getGeminiClient: vi.fn(),
+      getPlanModeHistoryStartIndex: vi.fn().mockReturnValue(0),
       storage: {
         getPlansDir: vi.fn().mockReturnValue(mockPlansDir),
       } as unknown as Config['storage'],
@@ -240,6 +243,49 @@ Read and follow the plan strictly during implementation.`,
       expect(mockConfig.setApprovedPlanPath).toHaveBeenCalledWith(expectedPath);
     });
 
+    it('should truncate history surgically when clearConversation is true', async () => {
+      const planRelativePath = createPlanFile('test.md', '# Content');
+      const invocation = tool.build({ plan_path: planRelativePath });
+
+      const mockSetHistory = vi.fn();
+      const mockHistory = [
+        { role: 'user', parts: [{ text: 'Pre-plan prompt' }] },
+        { role: 'model', parts: [{ text: 'Pre-plan response' }] },
+        { role: 'user', parts: [{ text: 'Enter plan mode' }] }, // Planning start turn (index 2)
+        { role: 'model', parts: [{ text: 'Draft 1' }] },
+        { role: 'user', parts: [{ text: 'No, change it' }] },
+        {
+          role: 'model',
+          parts: [{ functionCall: { name: 'exit_plan_mode', args: {} } }],
+        },
+      ];
+      vi.mocked(mockConfig.getGeminiClient!).mockReturnValue({
+        getHistory: vi.fn().mockReturnValue(mockHistory),
+        setHistory: mockSetHistory,
+      } as unknown as GeminiClient);
+      vi.mocked(mockConfig.getPlanModeHistoryStartIndex!).mockReturnValue(2);
+
+      const confirmDetails = await invocation.shouldConfirmExecute(
+        new AbortController().signal,
+      );
+      if (confirmDetails === false) return;
+
+      await confirmDetails.onConfirm(ToolConfirmationOutcome.ProceedOnce, {
+        approved: true,
+        approvalMode: ApprovalMode.AUTO_EDIT,
+        clearConversation: true,
+      });
+
+      await invocation.execute(new AbortController().signal);
+
+      expect(mockSetHistory).toHaveBeenCalledWith([
+        mockHistory[0], // pre-plan user
+        mockHistory[1], // pre-plan model
+        mockHistory[2], // first planning user message
+        mockHistory[5], // last model message (exit_plan_mode)
+      ]);
+    });
+
     it('should return feedback message when plan is rejected with feedback', async () => {
       const planRelativePath = createPlanFile('test.md', '# Content');
       const invocation = tool.build({ plan_path: planRelativePath });

packages/core/src/tools/exit-plan-mode.ts

@@ -214,6 +214,34 @@ export class ExitPlanModeInvocation extends BaseToolInvocation<
       this.config.setApprovalMode(newMode);
       this.config.setApprovedPlanPath(resolvedPlanPath);
 
+      if (payload.clearConversation) {
+        const geminiClient = this.config.getGeminiClient();
+        if (geminiClient) {
+          const history = geminiClient.getHistory();
+          const startIndex = this.config.getPlanModeHistoryStartIndex();
+
+          // Find the first user message at or after the start index.
+          // This represents the beginning of the current planning phase.
+          let planningUserIndex = -1;
+          for (let i = startIndex; i < history.length - 1; i++) {
+            if (history[i].role === 'user') {
+              planningUserIndex = i;
+              break;
+            }
+          }
+
+          if (planningUserIndex !== -1) {
+            const lastModelMessage = history[history.length - 1];
+            // Keep everything before the plan, plus the initial plan request turn.
+            const newHistory = [
+              ...history.slice(0, planningUserIndex + 1),
+              lastModelMessage,
+            ];
+            geminiClient.setHistory(newHistory);
+          }
+        }
+      }
+
       logPlanExecution(this.config, new PlanExecutionEvent(newMode));
 
       const exitMessage = getPlanModeExitMessage(newMode);

packages/core/src/tools/tools.ts

@@ -757,6 +757,8 @@ export interface ToolExitPlanModeConfirmationPayload {
   approvalMode?: ApprovalMode;
   /** If rejected, the user's feedback */
   feedback?: string;
+  /** If the user wants to clear the conversation context upon approval */
+  clearConversation?: boolean;
 }
 
 export type ToolConfirmationPayload =

packages/core/src/utils/events.ts

@@ -9,6 +9,7 @@ import type { AgentDefinition } from '../agents/types.js';
 import type { McpClient } from '../tools/mcp-client.js';
 import type { ExtensionEvents } from './extensionLoader.js';
 import type { EditorType } from './editor.js';
+import type { ApprovalMode } from '../policy/types.js';
 import type {
   TokenStorageInitializationEvent,
   KeychainAvailabilityEvent,
@@ -52,6 +53,16 @@ export interface ModelChangedPayload {
   model: string;
 }
 
+/**
+ * Payload for the 'approval-mode-changed' event.
+ */
+export interface ApprovalModeChangedPayload {
+  /**
+   * The new approval mode that was set.
+   */
+  mode: ApprovalMode;
+}
+
 /**
  * Payload for the 'console-log' event.
  */
@@ -167,6 +178,7 @@ export interface QuotaChangedPayload {
 export enum CoreEvent {
   UserFeedback = 'user-feedback',
   ModelChanged = 'model-changed',
+  ApprovalModeChanged = 'approval-mode-changed',
   ConsoleLog = 'console-log',
   Output = 'output',
   MemoryChanged = 'memory-changed',
@@ -200,6 +212,7 @@ export interface EditorSelectedPayload {
 export interface CoreEvents extends ExtensionEvents {
   [CoreEvent.UserFeedback]: [UserFeedbackPayload];
   [CoreEvent.ModelChanged]: [ModelChangedPayload];
+  [CoreEvent.ApprovalModeChanged]: [ApprovalModeChangedPayload];
   [CoreEvent.ConsoleLog]: [ConsoleLogPayload];
   [CoreEvent.Output]: [OutputPayload];
   [CoreEvent.MemoryChanged]: [MemoryChangedPayload];
@@ -301,6 +314,14 @@ export class CoreEventEmitter extends EventEmitter<CoreEvents> {
     this.emit(CoreEvent.ModelChanged, payload);
   }
 
+  /**
+   * Notifies subscribers that the approval mode has changed.
+   */
+  emitApprovalModeChanged(mode: ApprovalMode): void {
+    const payload: ApprovalModeChangedPayload = { mode };
+    this.emit(CoreEvent.ApprovalModeChanged, payload);
+  }
+
   /**
    * Notifies subscribers that settings have been modified.
    */