feat: save checkpoints immediately when users submit messages

- Move checkpoint saving from recursivelyMakeClineRequests to handleWebviewAskResponse
- Checkpoints are now saved when users click send, not when API requests are made
- This allows users to easily revert to the state right before they typed their message
- Update tests to reflect the new checkpoint behavior
- Make handleWebviewAskResponse async to support checkpoint saving

src/core/task/Task.ts

@@ -741,7 +741,21 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 		this.handleWebviewAskResponse("messageResponse", text, images)
 	}
 
-	handleWebviewAskResponse(askResponse: ClineAskResponse, text?: string, images?: string[]) {
+	async handleWebviewAskResponse(askResponse: ClineAskResponse, text?: string, images?: string[]) {
+		// Save checkpoint immediately when user submits a message
+		// This allows users to easily revert to the state right before they typed their message
+		if (this.enableCheckpoints && askResponse === "messageResponse") {
+			try {
+				await this.checkpointSave(true)
+			} catch (error) {
+				console.error(
+					`[Task#handleWebviewAskResponse] Error saving checkpoint before user message: ${error.message}`,
+					error,
+				)
+				// Don't block the user message if checkpoint fails
+			}
+		}
+
 		this.askResponse = askResponse
 		this.askResponseText = text
 		this.askResponseImages = images
@@ -1533,17 +1547,9 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 		// results.
 		const finalUserContent = [...parsedUserContent, { type: "text" as const, text: environmentDetails }]
 
-		// Save checkpoint before adding user message to conversation history
-		if (this.enableCheckpoints) {
-			try {
-				await this.checkpointSave(true)
-			} catch (error) {
-				console.error(
-					`[Task#recursivelyMakeClineRequests] Error saving checkpoint before user message: ${error.message}`,
-					error,
-				)
-			}
-		}
+		// Note: Checkpoint is now saved in handleWebviewAskResponse when user submits a message,
+		// not here before the API request. This allows users to easily revert to the state
+		// right before they typed their message.
 
 		await this.addToApiConversationHistory({ role: "user", content: finalUserContent })
 		TelemetryService.instance.captureConversationMessage(this.taskId, "user")

src/core/task/__tests__/Task.spec.ts

@@ -1615,7 +1615,7 @@ describe("Cline", () => {
 		})
 
 		describe("Checkpoint before user messages", () => {
-			it("should save checkpoint before adding user message to conversation history", async () => {
+			it("should save checkpoint when user submits a message via handleWebviewAskResponse", async () => {
 				const task = new Task({
 					provider: mockProvider,
 					apiConfiguration: mockApiConfig,
@@ -1627,39 +1627,41 @@ describe("Cline", () => {
 				// Mock checkpointSave method
 				const checkpointSaveSpy = vi.spyOn(task, "checkpointSave").mockResolvedValue(undefined)
 
-				// Mock addToApiConversationHistory
-				const addToApiConversationHistorySpy = vi
-					.spyOn(task as any, "addToApiConversationHistory")
-					.mockResolvedValue(undefined)
+				// Call handleWebviewAskResponse with a user message
+				await task.handleWebviewAskResponse("messageResponse", "test user message", ["image.png"])
 
-				// Mock other required methods
-				vi.spyOn(task as any, "saveClineMessages").mockResolvedValue(undefined)
-				vi.spyOn(task.api, "createMessage").mockReturnValue({
-					async *[Symbol.asyncIterator]() {
-						yield { type: "text", text: "response" }
-					},
-				} as any)
-
-				// Mock clineMessages to avoid errors
-				task.clineMessages = [
-					{
-						ts: Date.now(),
-						type: "say",
-						say: "api_req_started",
-						text: JSON.stringify({ request: "test" }),
-					},
-				]
-
-				// Call recursivelyMakeClineRequests which should trigger checkpoint save
-				await task.recursivelyMakeClineRequests([{ type: "text", text: "test user message" }])
-
-				// Verify checkpoint was saved before adding to conversation history
+				// Verify checkpoint was saved
 				expect(checkpointSaveSpy).toHaveBeenCalledWith(true)
-				expect(checkpointSaveSpy).toHaveBeenCalledBefore(addToApiConversationHistorySpy)
-				expect(addToApiConversationHistorySpy).toHaveBeenCalled()
+
+				// Verify the response was set
+				expect(task["askResponse"]).toBe("messageResponse")
+				expect(task["askResponseText"]).toBe("test user message")
+				expect(task["askResponseImages"]).toEqual(["image.png"])
 			})
 
-			it("should handle checkpoint save errors gracefully", async () => {
+			it("should not save checkpoint for non-messageResponse ask responses", async () => {
+				const task = new Task({
+					provider: mockProvider,
+					apiConfiguration: mockApiConfig,
+					task: "test task",
+					enableCheckpoints: true,
+					startTask: false,
+				})
+
+				// Mock checkpointSave method
+				const checkpointSaveSpy = vi.spyOn(task, "checkpointSave").mockResolvedValue(undefined)
+
+				// Call handleWebviewAskResponse with a non-message response
+				await task.handleWebviewAskResponse("yesButtonClicked", undefined, undefined)
+
+				// Verify checkpoint was NOT saved
+				expect(checkpointSaveSpy).not.toHaveBeenCalled()
+
+				// Verify the response was set
+				expect(task["askResponse"]).toBe("yesButtonClicked")
+			})
+
+			it("should handle checkpoint save errors gracefully in handleWebviewAskResponse", async () => {
 				const task = new Task({
 					provider: mockProvider,
 					apiConfiguration: mockApiConfig,
@@ -1675,31 +1677,8 @@ describe("Cline", () => {
 				// Mock console.error to verify error logging
 				const consoleErrorSpy = vi.spyOn(console, "error").mockImplementation(() => {})
 
-				// Mock addToApiConversationHistory to verify it still gets called
-				const addToApiConversationHistorySpy = vi
-					.spyOn(task as any, "addToApiConversationHistory")
-					.mockResolvedValue(undefined)
-
-				// Mock other required methods
-				vi.spyOn(task as any, "saveClineMessages").mockResolvedValue(undefined)
-				vi.spyOn(task.api, "createMessage").mockReturnValue({
-					async *[Symbol.asyncIterator]() {
-						yield { type: "text", text: "response" }
-					},
-				} as any)
-
-				// Mock clineMessages
-				task.clineMessages = [
-					{
-						ts: Date.now(),
-						type: "say",
-						say: "api_req_started",
-						text: JSON.stringify({ request: "test" }),
-					},
-				]
-
-				// Call recursivelyMakeClineRequests
-				await task.recursivelyMakeClineRequests([{ type: "text", text: "test user message" }])
+				// Call handleWebviewAskResponse
+				await task.handleWebviewAskResponse("messageResponse", "test user message", ["image.png"])
 
 				// Verify checkpoint save was attempted
 				expect(checkpointSaveSpy).toHaveBeenCalledWith(true)
@@ -1710,8 +1689,10 @@ describe("Cline", () => {
 					checkpointError,
 				)
 
-				// Verify conversation history was still updated despite checkpoint error
-				expect(addToApiConversationHistorySpy).toHaveBeenCalled()
+				// Verify the response was still set despite checkpoint error
+				expect(task["askResponse"]).toBe("messageResponse")
+				expect(task["askResponseText"]).toBe("test user message")
+				expect(task["askResponseImages"]).toEqual(["image.png"])
 
 				// Restore console.error
 				consoleErrorSpy.mockRestore()
@@ -1729,6 +1710,30 @@ describe("Cline", () => {
 				// Mock checkpointSave method
 				const checkpointSaveSpy = vi.spyOn(task, "checkpointSave").mockResolvedValue(undefined)
 
+				// Call handleWebviewAskResponse with a user message
+				await task.handleWebviewAskResponse("messageResponse", "test user message", ["image.png"])
+
+				// Verify checkpoint was NOT saved
+				expect(checkpointSaveSpy).not.toHaveBeenCalled()
+
+				// Verify the response was still set
+				expect(task["askResponse"]).toBe("messageResponse")
+				expect(task["askResponseText"]).toBe("test user message")
+				expect(task["askResponseImages"]).toEqual(["image.png"])
+			})
+
+			it("should not save checkpoint in recursivelyMakeClineRequests anymore", async () => {
+				const task = new Task({
+					provider: mockProvider,
+					apiConfiguration: mockApiConfig,
+					task: "test task",
+					enableCheckpoints: true,
+					startTask: false,
+				})
+
+				// Mock checkpointSave method
+				const checkpointSaveSpy = vi.spyOn(task, "checkpointSave").mockResolvedValue(undefined)
+
 				// Mock other required methods
 				vi.spyOn(task as any, "addToApiConversationHistory").mockResolvedValue(undefined)
 				vi.spyOn(task as any, "saveClineMessages").mockResolvedValue(undefined)
@@ -1751,7 +1756,8 @@ describe("Cline", () => {
 				// Call recursivelyMakeClineRequests
 				await task.recursivelyMakeClineRequests([{ type: "text", text: "test user message" }])
 
-				// Verify checkpoint was NOT saved
+				// Verify checkpoint was NOT saved in recursivelyMakeClineRequests
+				// (it should only be saved in handleWebviewAskResponse now)
 				expect(checkpointSaveSpy).not.toHaveBeenCalled()
 			})
 		})

src/core/webview/webviewMessageHandler.ts

@@ -346,7 +346,10 @@ export const webviewMessageHandler = async (
 			await provider.postStateToWebview()
 			break
 		case "askResponse":
-			provider.getCurrentCline()?.handleWebviewAskResponse(message.askResponse!, message.text, message.images)
+			// handleWebviewAskResponse is now async to support checkpoint saving
+			await provider
+				.getCurrentCline()
+				?.handleWebviewAskResponse(message.askResponse!, message.text, message.images)
 			break
 		case "autoCondenseContext":
 			await updateGlobalState("autoCondenseContext", message.bool)