diff --git a/src/core/task/Task.ts b/src/core/task/Task.ts
index 2103dacb274..b8e2ba00f80 100644
--- a/src/core/task/Task.ts
+++ b/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
@@ -1533,6 +1547,10 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 		// results.
 		const finalUserContent = [...parsedUserContent, { type: "text" as const, text: environmentDetails }]
 
+		// 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")
 
diff --git a/src/core/task/__tests__/Task.spec.ts b/src/core/task/__tests__/Task.spec.ts
index 39df433814b..c3e90f7a104 100644
--- a/src/core/task/__tests__/Task.spec.ts
+++ b/src/core/task/__tests__/Task.spec.ts
@@ -1613,5 +1613,153 @@ describe("Cline", () => {
 				consoleErrorSpy.mockRestore()
 			})
 		})
+
+		describe("Checkpoint before user messages", () => {
+			it("should save checkpoint when user submits a message via handleWebviewAskResponse", 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 user message
+				await task.handleWebviewAskResponse("messageResponse", "test user message", ["image.png"])
+
+				// Verify checkpoint was saved
+				expect(checkpointSaveSpy).toHaveBeenCalledWith(true)
+
+				// 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 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,
+					task: "test task",
+					enableCheckpoints: true,
+					startTask: false,
+				})
+
+				// Mock checkpointSave to throw an error
+				const checkpointError = new Error("Checkpoint save failed")
+				const checkpointSaveSpy = vi.spyOn(task, "checkpointSave").mockRejectedValue(checkpointError)
+
+				// Mock console.error to verify error logging
+				const consoleErrorSpy = vi.spyOn(console, "error").mockImplementation(() => {})
+
+				// Call handleWebviewAskResponse
+				await task.handleWebviewAskResponse("messageResponse", "test user message", ["image.png"])
+
+				// Verify checkpoint save was attempted
+				expect(checkpointSaveSpy).toHaveBeenCalledWith(true)
+
+				// Verify error was logged
+				expect(consoleErrorSpy).toHaveBeenCalledWith(
+					expect.stringContaining("Error saving checkpoint before user message"),
+					checkpointError,
+				)
+
+				// 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()
+			})
+
+			it("should not save checkpoint when checkpoints are disabled", async () => {
+				const task = new Task({
+					provider: mockProvider,
+					apiConfiguration: mockApiConfig,
+					task: "test task",
+					enableCheckpoints: false,
+					startTask: false,
+				})
+
+				// 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)
+				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" }])
+
+				// Verify checkpoint was NOT saved in recursivelyMakeClineRequests
+				// (it should only be saved in handleWebviewAskResponse now)
+				expect(checkpointSaveSpy).not.toHaveBeenCalled()
+			})
+		})
 	})
 })
diff --git a/src/core/webview/webviewMessageHandler.ts b/src/core/webview/webviewMessageHandler.ts
index 7e25ae14dcd..76f3ae09c57 100644
--- a/src/core/webview/webviewMessageHandler.ts
+++ b/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)