fix: handle pending ask operations during checkpoint restore

- Add handleWebviewAskResponse call before checkpoint restore to resolve any pending ask promises
- This prevents "Current ask promise was ignored" errors when restoring checkpoints
- Add comprehensive tests for pending ask scenarios

Fixes #8177

src/core/webview/__tests__/checkpointRestoreHandler.spec.ts

@@ -30,6 +30,8 @@ describe("checkpointRestoreHandler", () => {
 				mockCline.abort = true
 			}),
 			checkpointRestore: vi.fn(),
+			handleWebviewAskResponse: vi.fn(),
+			lastMessageTs: undefined,
 			clineMessages: [
 				{ ts: 1, type: "user", say: "user", text: "First message" },
 				{ ts: 2, type: "assistant", say: "assistant", text: "Response" },
@@ -238,5 +240,75 @@ describe("checkpointRestoreHandler", () => {
 				"Error during checkpoint restore: Checkpoint restore failed",
 			)
 		})
+
+		it("should handle pending ask operations before checkpoint restore", async () => {
+			// Simulate a pending ask operation
+			mockCline.lastMessageTs = Date.now()
+
+			await handleCheckpointRestoreOperation({
+				provider: mockProvider,
+				currentCline: mockCline,
+				messageTs: 3,
+				messageIndex: 2,
+				checkpoint: { hash: "abc123" },
+				operation: "delete",
+			})
+
+			// Verify handleWebviewAskResponse was called to resolve pending ask
+			expect(mockCline.handleWebviewAskResponse).toHaveBeenCalledWith("messageResponse", "", undefined)
+
+			// Verify checkpoint restore was still called
+			expect(mockCline.checkpointRestore).toHaveBeenCalled()
+		})
+
+		it("should handle pending ask operations for edit operations", async () => {
+			// Simulate a pending ask operation
+			mockCline.lastMessageTs = Date.now()
+
+			const editData = {
+				editedContent: "Edited content",
+				images: [],
+				apiConversationHistoryIndex: 2,
+			}
+
+			await handleCheckpointRestoreOperation({
+				provider: mockProvider,
+				currentCline: mockCline,
+				messageTs: 3,
+				messageIndex: 2,
+				checkpoint: { hash: "abc123" },
+				operation: "edit",
+				editData,
+			})
+
+			// Verify handleWebviewAskResponse was called to resolve pending ask
+			expect(mockCline.handleWebviewAskResponse).toHaveBeenCalledWith("messageResponse", "", undefined)
+
+			// Verify checkpoint restore was still called
+			expect(mockCline.checkpointRestore).toHaveBeenCalled()
+
+			// Verify pending edit operation was set
+			expect(mockProvider.setPendingEditOperation).toHaveBeenCalled()
+		})
+
+		it("should not call handleWebviewAskResponse if no pending ask", async () => {
+			// No pending ask operation (lastMessageTs is undefined)
+			mockCline.lastMessageTs = undefined
+
+			await handleCheckpointRestoreOperation({
+				provider: mockProvider,
+				currentCline: mockCline,
+				messageTs: 3,
+				messageIndex: 2,
+				checkpoint: { hash: "abc123" },
+				operation: "delete",
+			})
+
+			// Verify handleWebviewAskResponse was NOT called
+			expect(mockCline.handleWebviewAskResponse).not.toHaveBeenCalled()
+
+			// Verify checkpoint restore was still called
+			expect(mockCline.checkpointRestore).toHaveBeenCalled()
+		})
 	})
 })

src/core/webview/checkpointRestoreHandler.ts

@@ -27,18 +27,27 @@ export async function handleCheckpointRestoreOperation(config: CheckpointRestore
 	const { provider, currentCline, messageTs, checkpoint, operation, editData } = config
 
 	try {
-		// For delete operations, ensure the task is properly aborted to handle any pending ask operations
+		// For both delete and edit operations, we need to handle any pending ask operations
 		// This prevents "Current ask promise was ignored" errors
-		// For edit operations, we don't abort because the checkpoint restore will handle it
-		if (operation === "delete" && currentCline && !currentCline.abort) {
-			currentCline.abortTask()
-			// Wait a bit for the abort to complete
-			await pWaitFor(() => currentCline.abort === true, {
-				timeout: 1000,
-				interval: 50,
-			}).catch(() => {
-				// Continue even if timeout - the abort flag should be set
-			})
+		if (currentCline) {
+			// Handle any pending ask operations by providing a response
+			// This unblocks any waiting ask promises before the checkpoint restore
+			if (currentCline.lastMessageTs) {
+				// Use the public method to set a response for any pending ask
+				currentCline.handleWebviewAskResponse("messageResponse", "", undefined)
+			}
+
+			// For delete operations, abort the task
+			if (operation === "delete" && !currentCline.abort) {
+				currentCline.abortTask()
+				// Wait a bit for the abort to complete
+				await pWaitFor(() => currentCline.abort === true, {
+					timeout: 1000,
+					interval: 50,
+				}).catch(() => {
+					// Continue even if timeout - the abort flag should be set
+				})
+			}
 		}
 
 		// For edit operations, set up pending edit data before restoration