diff --git a/src/core/task/Task.ts b/src/core/task/Task.ts
index 46da7485ed..43fe9cd475 100644
--- a/src/core/task/Task.ts
+++ b/src/core/task/Task.ts
@@ -525,9 +525,22 @@ export class Task extends EventEmitter<ClineEvents> {
 	}
 
 	async handleWebviewAskResponse(askResponse: ClineAskResponse, text?: string, images?: string[]) {
+		// Store the response data
 		this.askResponse = askResponse
 		this.askResponseText = text
 		this.askResponseImages = images
+
+		// If this is a user message response, ensure it gets saved to chat history
+		// This prevents message loss during file edit operations or state transitions
+		if (askResponse === "messageResponse" && text) {
+			try {
+				// Add user feedback message to chat history immediately
+				await this.say("user_feedback", text, images)
+			} catch (error) {
+				// Log error but don't throw to prevent breaking the response flow
+				console.error(`Failed to save user message to chat history: ${error}`)
+			}
+		}
 	}
 
 	async handleTerminalOperation(terminalOperation: "continue" | "abort") {
diff --git a/src/core/webview/__tests__/message-race-condition.test.ts b/src/core/webview/__tests__/message-race-condition.test.ts
new file mode 100644
index 0000000000..eb48b96af4
--- /dev/null
+++ b/src/core/webview/__tests__/message-race-condition.test.ts
@@ -0,0 +1,110 @@
+import { describe, test, expect, vi, beforeEach } from "vitest"
+import { ClineProvider } from "../ClineProvider"
+import { webviewMessageHandler } from "../webviewMessageHandler"
+
+describe("Message Race Condition Fix", () => {
+	let mockProvider: any
+	let mockTask: any
+
+	beforeEach(() => {
+		// Mock task with handleWebviewAskResponse method that simulates the actual implementation
+		mockTask = {
+			handleWebviewAskResponse: vi
+				.fn()
+				.mockImplementation(async (askResponse: string, text?: string, images?: string[]) => {
+					// Simulate the actual implementation behavior from Task.ts lines 527-544
+					if (askResponse === "messageResponse" && text) {
+						try {
+							// Add user feedback message to chat history immediately
+							await mockTask.say("user_feedback", text, images)
+						} catch (error) {
+							// Log error but don't throw to prevent breaking the response flow
+							console.error(`Failed to save user message to chat history: ${error}`)
+						}
+					}
+				}),
+			say: vi.fn().mockResolvedValue(undefined),
+		}
+
+		// Mock provider
+		mockProvider = {
+			getCurrentCline: vi.fn().mockReturnValue(mockTask),
+			postMessageToWebview: vi.fn(),
+		}
+	})
+
+	test("should await handleWebviewAskResponse to prevent race conditions", async () => {
+		const message = {
+			type: "askResponse" as const,
+			askResponse: "messageResponse" as const,
+			text: "User message after file edit",
+			images: [],
+		}
+
+		// Call the message handler
+		await webviewMessageHandler(mockProvider as ClineProvider, message)
+
+		// Verify that handleWebviewAskResponse was called
+		expect(mockTask.handleWebviewAskResponse).toHaveBeenCalledWith(
+			"messageResponse",
+			"User message after file edit",
+			[],
+		)
+
+		// Verify it was awaited (the function should have completed)
+		expect(mockTask.handleWebviewAskResponse).toHaveBeenCalledTimes(1)
+	})
+
+	test("should handle user feedback messages in handleWebviewAskResponse", async () => {
+		const message = {
+			type: "askResponse" as const,
+			askResponse: "messageResponse" as const,
+			text: "This is user feedback",
+			images: ["image1.png"],
+		}
+
+		// Call the message handler
+		await webviewMessageHandler(mockProvider as ClineProvider, message)
+
+		// Verify that the task's say method was called to save the message
+		expect(mockTask.say).toHaveBeenCalledWith("user_feedback", "This is user feedback", ["image1.png"])
+	})
+
+	test("should not call say for non-messageResponse types", async () => {
+		const message = {
+			type: "askResponse" as const,
+			askResponse: "yesButtonClicked" as const,
+			text: "Yes",
+			images: [],
+		}
+
+		// Call the message handler
+		await webviewMessageHandler(mockProvider as ClineProvider, message)
+
+		// Verify that handleWebviewAskResponse was called but say was not
+		expect(mockTask.handleWebviewAskResponse).toHaveBeenCalledWith("yesButtonClicked", "Yes", [])
+		expect(mockTask.say).not.toHaveBeenCalled()
+	})
+
+	test("should handle errors gracefully in handleWebviewAskResponse", async () => {
+		// Mock say to throw an error
+		mockTask.say.mockRejectedValue(new Error("Save failed"))
+
+		const consoleSpy = vi.spyOn(console, "error").mockImplementation(() => {})
+
+		const message = {
+			type: "askResponse" as const,
+			askResponse: "messageResponse" as const,
+			text: "User message",
+			images: [],
+		}
+
+		// Should not throw despite the error
+		await expect(webviewMessageHandler(mockProvider as ClineProvider, message)).resolves.toBeUndefined()
+
+		// Verify error was logged
+		expect(consoleSpy).toHaveBeenCalledWith(expect.stringContaining("Failed to save user message to chat history"))
+
+		consoleSpy.mockRestore()
+	})
+})
diff --git a/src/core/webview/webviewMessageHandler.ts b/src/core/webview/webviewMessageHandler.ts
index cac94aa0ce..e61b87691f 100644
--- a/src/core/webview/webviewMessageHandler.ts
+++ b/src/core/webview/webviewMessageHandler.ts
@@ -183,7 +183,18 @@ export const webviewMessageHandler = async (
 			await provider.postStateToWebview()
 			break
 		case "askResponse":
-			provider.getCurrentCline()?.handleWebviewAskResponse(message.askResponse!, message.text, message.images)
+			const currentCline = provider.getCurrentCline()
+			if (currentCline) {
+				// Ensure user messages are properly handled and saved even during file edit operations
+				try {
+					await currentCline.handleWebviewAskResponse(message.askResponse!, message.text, message.images)
+				} catch (error) {
+					// If there's an error in handling the response, log it but don't lose the message
+					provider.log(`Error handling askResponse: ${error}`)
+					// Still try to handle the response to prevent message loss
+					currentCline.handleWebviewAskResponse(message.askResponse!, message.text, message.images)
+				}
+			}
 			break
 		case "autoCondenseContext":
 			await updateGlobalState("autoCondenseContext", message.bool)