diff --git a/src/core/checkpoints/__tests__/checkpointAfterDelete.test.ts b/src/core/checkpoints/__tests__/checkpointAfterDelete.test.ts
new file mode 100644
index 0000000000..8984f92d5c
--- /dev/null
+++ b/src/core/checkpoints/__tests__/checkpointAfterDelete.test.ts
@@ -0,0 +1,169 @@
+import { describe, it, expect, vi, beforeEach, afterEach } from "vitest"
+import { Task } from "../../task/Task"
+import { ClineProvider } from "../../webview/ClineProvider"
+import { checkpointSave } from "../index"
+import * as vscode from "vscode"
+
+// Mock vscode
+vi.mock("vscode", () => ({
+	window: {
+		showErrorMessage: vi.fn(),
+	},
+	Uri: {
+		file: vi.fn((path: string) => ({ fsPath: path })),
+	},
+}))
+
+// Mock other dependencies
+vi.mock("@roo-code/telemetry", () => ({
+	TelemetryService: {
+		instance: {
+			captureCheckpointCreated: vi.fn(),
+		},
+	},
+}))
+
+vi.mock("../../../utils/path", () => ({
+	getWorkspacePath: vi.fn(() => "/test/workspace"),
+}))
+
+describe("Checkpoint after message deletion", () => {
+	let mockProvider: any
+	let mockTask: any
+	let mockCheckpointService: any
+
+	beforeEach(() => {
+		// Create mock checkpoint service
+		mockCheckpointService = {
+			isInitialized: false,
+			saveCheckpoint: vi.fn().mockResolvedValue({ commit: "test-commit-hash" }),
+			on: vi.fn(),
+			initShadowGit: vi.fn().mockResolvedValue(undefined),
+		}
+
+		// Create mock provider
+		mockProvider = {
+			context: {
+				globalStorageUri: { fsPath: "/test/storage" },
+			},
+			log: vi.fn(),
+			postMessageToWebview: vi.fn(),
+			postStateToWebview: vi.fn(),
+		}
+
+		// Create mock task
+		mockTask = {
+			taskId: "test-task-id",
+			enableCheckpoints: true,
+			checkpointService: undefined,
+			checkpointServiceInitializing: false,
+			providerRef: {
+				deref: () => mockProvider,
+			},
+			clineMessages: [],
+			pendingUserMessageCheckpoint: undefined,
+		}
+
+		// Mock the RepoPerTaskCheckpointService.create to return our mock
+		vi.mock("../../../services/checkpoints", () => ({
+			RepoPerTaskCheckpointService: {
+				create: vi.fn(() => mockCheckpointService),
+			},
+		}))
+	})
+
+	afterEach(() => {
+		vi.clearAllMocks()
+	})
+
+	it("should wait for checkpoint service initialization before saving", async () => {
+		// Simulate service initialization after a delay
+		setTimeout(() => {
+			mockCheckpointService.isInitialized = true
+		}, 100)
+
+		// Call checkpointSave
+		const savePromise = checkpointSave(mockTask, true)
+
+		// Initially, service should not be initialized
+		expect(mockCheckpointService.isInitialized).toBe(false)
+
+		// Wait for the save to complete
+		const result = await savePromise
+
+		// Service should now be initialized
+		expect(mockCheckpointService.isInitialized).toBe(true)
+
+		// saveCheckpoint should have been called
+		expect(mockCheckpointService.saveCheckpoint).toHaveBeenCalledWith(
+			expect.stringContaining("Task: test-task-id"),
+			{ allowEmpty: true },
+		)
+
+		// Result should contain the commit hash
+		expect(result).toEqual({ commit: "test-commit-hash" })
+
+		// Task should still have checkpoints enabled
+		expect(mockTask.enableCheckpoints).toBe(true)
+	})
+
+	it("should handle timeout when service doesn't initialize", async () => {
+		// Service never initializes
+		mockCheckpointService.isInitialized = false
+
+		// Call checkpointSave with a task that has no checkpoint service
+		const taskWithNoService = {
+			...mockTask,
+			checkpointService: undefined,
+			enableCheckpoints: false,
+		}
+
+		const result = await checkpointSave(taskWithNoService, true)
+
+		// Result should be undefined
+		expect(result).toBeUndefined()
+
+		// saveCheckpoint should not have been called
+		expect(mockCheckpointService.saveCheckpoint).not.toHaveBeenCalled()
+	})
+
+	it("should preserve checkpoint data through message deletion flow", async () => {
+		// Initialize service
+		mockCheckpointService.isInitialized = true
+
+		// Simulate saving checkpoint before user message
+		const checkpointResult = await checkpointSave(mockTask, true)
+		expect(checkpointResult).toEqual({ commit: "test-commit-hash" })
+
+		// Simulate setting pendingUserMessageCheckpoint
+		if (checkpointResult && "commit" in checkpointResult) {
+			mockTask.pendingUserMessageCheckpoint = {
+				hash: checkpointResult.commit,
+				timestamp: Date.now(),
+				type: "user_message",
+			}
+		}
+
+		// Verify checkpoint data is preserved
+		expect(mockTask.pendingUserMessageCheckpoint).toBeDefined()
+		expect(mockTask.pendingUserMessageCheckpoint.hash).toBe("test-commit-hash")
+
+		// Simulate message deletion and reinitialization
+		mockTask.clineMessages = []
+		mockTask.checkpointService = undefined
+		mockTask.checkpointServiceInitializing = false
+
+		// Re-initialize checkpoint service
+		setTimeout(() => {
+			mockCheckpointService.isInitialized = true
+			mockTask.checkpointService = mockCheckpointService
+		}, 50)
+
+		// Save checkpoint again after deletion
+		const newCheckpointResult = await checkpointSave(mockTask, true)
+
+		// Should still work after reinitialization
+		expect(newCheckpointResult).toEqual({ commit: "test-commit-hash" })
+		expect(mockTask.enableCheckpoints).toBe(true)
+	})
+})
diff --git a/src/core/checkpoints/index.ts b/src/core/checkpoints/index.ts
index dcbe796eb7..cf0cb61f5e 100644
--- a/src/core/checkpoints/index.ts
+++ b/src/core/checkpoints/index.ts
@@ -150,19 +150,13 @@ async function getInitializedCheckpointService(
 }
 
 export async function checkpointSave(cline: Task, force = false) {
-	const service = getCheckpointService(cline)
+	// Use getInitializedCheckpointService to wait for initialization
+	const service = await getInitializedCheckpointService(cline)
 
 	if (!service) {
 		return
 	}
 
-	if (!service.isInitialized) {
-		const provider = cline.providerRef.deref()
-		provider?.log("[checkpointSave] checkpoints didn't initialize in time, disabling checkpoints for this task")
-		cline.enableCheckpoints = false
-		return
-	}
-
 	TelemetryService.instance.captureCheckpointCreated(cline.taskId)
 
 	// Start the checkpoint process in the background.
@@ -176,9 +170,13 @@ export type CheckpointRestoreOptions = {
 	ts: number
 	commitHash: string
 	mode: "preview" | "restore"
+	operation?: "delete" | "edit" // Optional to maintain backward compatibility
 }
 
-export async function checkpointRestore(cline: Task, { ts, commitHash, mode }: CheckpointRestoreOptions) {
+export async function checkpointRestore(
+	cline: Task,
+	{ ts, commitHash, mode, operation = "delete" }: CheckpointRestoreOptions,
+) {
 	const service = await getInitializedCheckpointService(cline)
 
 	if (!service) {
@@ -207,7 +205,10 @@ export async function checkpointRestore(cline: Task, { ts, commitHash, mode }: C
 				cline.combineMessages(deletedMessages),
 			)
 
-			await cline.overwriteClineMessages(cline.clineMessages.slice(0, index + 1))
+			// For delete operations, exclude the checkpoint message itself
+			// For edit operations, include the checkpoint message (to be edited)
+			const endIndex = operation === "edit" ? index + 1 : index
+			await cline.overwriteClineMessages(cline.clineMessages.slice(0, endIndex))
 
 			// TODO: Verify that this is working as expected.
 			await cline.say(
diff --git a/src/core/task/Task.ts b/src/core/task/Task.ts
index 389c395e99..16d88e4834 100644
--- a/src/core/task/Task.ts
+++ b/src/core/task/Task.ts
@@ -552,39 +552,10 @@ export class Task extends EventEmitter<ClineEvents> {
 	}
 
 	async handleWebviewAskResponse(askResponse: ClineAskResponse, text?: string, images?: string[]) {
-		// Save checkpoint BEFORE setting the response to ensure it's ready when the user_feedback message is created
-		if (this.enableCheckpoints && askResponse === "messageResponse") {
-			console.log("[Task#handleWebviewAskResponse] Saving checkpoint for user message")
-			try {
-				const checkpointResult = await this.checkpointSave(true) // Force checkpoint save
-				console.log("[Task#handleWebviewAskResponse] Checkpoint result:", checkpointResult)
-				if (checkpointResult?.commit) {
-					// Store checkpoint data temporarily to be used when creating the user_feedback message
-					this.pendingUserMessageCheckpoint = {
-						hash: checkpointResult.commit,
-						timestamp: Date.now(),
-						type: "user_message",
-					}
-					console.log(
-						"[Task#handleWebviewAskResponse] Set pendingUserMessageCheckpoint:",
-						this.pendingUserMessageCheckpoint,
-					)
-				} else {
-					console.log("[Task#handleWebviewAskResponse] No commit in checkpoint result")
-				}
-			} catch (error) {
-				console.error("[Task#handleWebviewAskResponse] Failed to save checkpoint after user message:", error)
-			}
-		} else {
-			console.log(
-				"[Task#handleWebviewAskResponse] Skipping checkpoint save - enableCheckpoints:",
-				this.enableCheckpoints,
-				"askResponse:",
-				askResponse,
-			)
-		}
+		// Checkpoint saving is now handled in webviewMessageHandler before this method is called
+		console.log("[Task#handleWebviewAskResponse] Processing askResponse:", askResponse)
 
-		// Now set the response, which will trigger the ask promise to resolve
+		// Set the response, which will trigger the ask promise to resolve
 		this.askResponse = askResponse
 		this.askResponseText = text
 		this.askResponseImages = images
diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index 1b7662c720..550d258d84 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -605,6 +605,54 @@ export class ClineProvider
 		this.log(
 			`[subtasks] ${cline.parentTask ? "child" : "parent"} task ${cline.taskId}.${cline.instanceId} instantiated`,
 		)
+
+		// Check if there's a pending edit after checkpoint restoration
+		if ((this as any).pendingEditAfterRestore) {
+			const pendingEdit = (this as any).pendingEditAfterRestore
+			;(this as any).pendingEditAfterRestore = undefined // Clear the pending edit
+
+			this.log(`[initClineWithHistoryItem] Processing pending edit after checkpoint restoration`)
+
+			// Process the pending edit after a short delay to ensure the task is fully initialized
+			setTimeout(async () => {
+				try {
+					// Find the message index in the restored state
+					const { messageIndex, apiConversationHistoryIndex } = (() => {
+						const messageIndex = cline.clineMessages.findIndex((msg) => msg.ts === pendingEdit.messageTs)
+						const apiConversationHistoryIndex = cline.apiConversationHistory.findIndex(
+							(msg) => msg.ts === pendingEdit.messageTs,
+						)
+						return { messageIndex, apiConversationHistoryIndex }
+					})()
+
+					if (messageIndex !== -1) {
+						// Remove the target message and all subsequent messages
+						await cline.overwriteClineMessages(cline.clineMessages.slice(0, messageIndex))
+
+						if (apiConversationHistoryIndex !== -1) {
+							await cline.overwriteApiConversationHistory(
+								cline.apiConversationHistory.slice(0, apiConversationHistoryIndex),
+							)
+						}
+
+						// If there was an original checkpoint, preserve it for the new message
+						if (pendingEdit.originalCheckpoint) {
+							cline.pendingUserMessageCheckpoint = pendingEdit.originalCheckpoint
+						}
+
+						// Process the edited message
+						await cline.handleWebviewAskResponse(
+							"messageResponse",
+							pendingEdit.editedContent,
+							pendingEdit.images,
+						)
+					}
+				} catch (error) {
+					this.log(`[initClineWithHistoryItem] Error processing pending edit: ${error}`)
+				}
+			}, 100) // Small delay to ensure task is fully ready
+		}
+
 		return cline
 	}
 
diff --git a/src/core/webview/__tests__/webviewMessageHandler.checkpoint.test.ts b/src/core/webview/__tests__/webviewMessageHandler.checkpoint.test.ts
new file mode 100644
index 0000000000..fe42abd11a
--- /dev/null
+++ b/src/core/webview/__tests__/webviewMessageHandler.checkpoint.test.ts
@@ -0,0 +1,150 @@
+import { describe, it, expect, vi, beforeEach } from "vitest"
+import { webviewMessageHandler } from "../webviewMessageHandler"
+import { saveTaskMessages } from "../../task-persistence"
+import { checkpointRestore } from "../../checkpoints"
+
+// Mock dependencies
+vi.mock("../../task-persistence")
+vi.mock("../../checkpoints")
+vi.mock("vscode", () => ({
+	window: {
+		showErrorMessage: vi.fn(),
+	},
+}))
+
+describe("webviewMessageHandler - checkpoint operations", () => {
+	let mockProvider: any
+	let mockCline: any
+
+	beforeEach(() => {
+		vi.clearAllMocks()
+
+		// Setup mock Cline instance
+		mockCline = {
+			taskId: "test-task-123",
+			clineMessages: [
+				{ ts: 1, type: "user", say: "user", text: "First message" },
+				{ ts: 2, type: "assistant", say: "assistant", text: "Response" },
+				{
+					ts: 3,
+					type: "user",
+					say: "user",
+					text: "Checkpoint message",
+					checkpoint: { hash: "abc123", label: "Test checkpoint" },
+				},
+				{ ts: 4, type: "assistant", say: "assistant", text: "After checkpoint" },
+			],
+			apiConversationHistory: [
+				{ ts: 1, role: "user", content: [{ type: "text", text: "First message" }] },
+				{ ts: 2, role: "assistant", content: [{ type: "text", text: "Response" }] },
+				{ ts: 3, role: "user", content: [{ type: "text", text: "Checkpoint message" }] },
+				{ ts: 4, role: "assistant", content: [{ type: "text", text: "After checkpoint" }] },
+			],
+			checkpointRestore: vi.fn(),
+			overwriteClineMessages: vi.fn(),
+			overwriteApiConversationHistory: vi.fn(),
+		}
+
+		// Setup mock provider
+		mockProvider = {
+			getCurrentCline: vi.fn(() => mockCline),
+			postMessageToWebview: vi.fn(),
+			getTaskWithId: vi.fn(() => ({
+				historyItem: { id: "test-task-123", messages: mockCline.clineMessages },
+			})),
+			initClineWithHistoryItem: vi.fn(),
+			contextProxy: {
+				globalStorageUri: { fsPath: "/test/storage" },
+			},
+		}
+	})
+
+	describe("delete operations with checkpoint restoration", () => {
+		it("should save messages to disk after checkpoint restoration", async () => {
+			// Simulate checkpoint restoration that removes messages
+			mockCline.checkpointRestore.mockImplementation(async () => {
+				// Simulate the effect of checkpoint restoration
+				mockCline.clineMessages = mockCline.clineMessages.slice(0, 2)
+			})
+
+			// Call the handler with delete confirmation
+			await webviewMessageHandler(mockProvider, {
+				type: "deleteMessageConfirm",
+				messageTs: 3,
+				restoreCheckpoint: true,
+			})
+
+			// Verify checkpoint restore was called with delete operation
+			expect(mockCline.checkpointRestore).toHaveBeenCalledWith({
+				ts: 3,
+				commitHash: "abc123",
+				mode: "restore",
+				operation: "delete",
+			})
+
+			// Verify saveTaskMessages was called after checkpoint restoration
+			expect(saveTaskMessages).toHaveBeenCalledWith({
+				messages: mockCline.clineMessages,
+				taskId: "test-task-123",
+				globalStoragePath: "/test/storage",
+			})
+
+			// Verify the save happened after the checkpoint restore
+			const checkpointRestoreOrder = mockCline.checkpointRestore.mock.invocationCallOrder[0]
+			const saveTaskMessagesOrder = (saveTaskMessages as any).mock.invocationCallOrder[0]
+			expect(saveTaskMessagesOrder).toBeGreaterThan(checkpointRestoreOrder)
+		})
+
+		it("should save messages for non-checkpoint deletes", async () => {
+			// Call the handler with delete confirmation (no checkpoint restoration)
+			await webviewMessageHandler(mockProvider, {
+				type: "deleteMessageConfirm",
+				messageTs: 2,
+				restoreCheckpoint: false,
+			})
+
+			// Verify saveTaskMessages was called
+			expect(saveTaskMessages).toHaveBeenCalledWith({
+				messages: expect.any(Array),
+				taskId: "test-task-123",
+				globalStoragePath: "/test/storage",
+			})
+
+			// Verify checkpoint restore was NOT called
+			expect(mockCline.checkpointRestore).not.toHaveBeenCalled()
+		})
+	})
+
+	describe("edit operations with checkpoint restoration", () => {
+		it("should call checkpoint restore with edit operation", async () => {
+			// Mock the pending edit storage
+			mockCline.pendingEditOperation = null
+
+			// Call the handler with edit confirmation
+			await webviewMessageHandler(mockProvider, {
+				type: "editMessageConfirm",
+				messageTs: 3,
+				text: "Edited checkpoint message",
+				restoreCheckpoint: true,
+			})
+
+			// Verify checkpoint restore was called with edit operation
+			expect(mockCline.checkpointRestore).toHaveBeenCalledWith({
+				ts: 3,
+				commitHash: "abc123",
+				mode: "restore",
+				operation: "edit",
+			})
+
+			// Verify the pending edit operation was stored
+			expect(mockCline.pendingEditOperation).toEqual({
+				messageTs: 3,
+				editedContent: "Edited checkpoint message",
+				images: undefined,
+				messageIndex: 2,
+				apiConversationHistoryIndex: 2,
+				originalCheckpoint: { hash: "abc123", label: "Test checkpoint" },
+			})
+		})
+	})
+})
diff --git a/src/core/webview/webviewMessageHandler.ts b/src/core/webview/webviewMessageHandler.ts
index 62e5e27fc8..682c46cc5e 100644
--- a/src/core/webview/webviewMessageHandler.ts
+++ b/src/core/webview/webviewMessageHandler.ts
@@ -16,6 +16,7 @@ import {
 import { CloudService } from "@roo-code/cloud"
 import { TelemetryService } from "@roo-code/telemetry"
 import { type ApiMessage } from "../task-persistence/apiMessages"
+import { saveTaskMessages } from "../task-persistence"
 
 import { ClineProvider } from "./ClineProvider"
 import { changeLanguage, t } from "../../i18n"
@@ -69,10 +70,10 @@ export const webviewMessageHandler = async (
 	 * Shared utility to find message indices based on timestamp
 	 */
 	const findMessageIndices = (messageTs: number, currentCline: any) => {
-		const timeCutoff = messageTs - 1000 // 1 second buffer before the message
-		const messageIndex = currentCline.clineMessages.findIndex((msg: ClineMessage) => msg.ts && msg.ts >= timeCutoff)
+		// Find the exact message by timestamp, not the first one after a cutoff
+		const messageIndex = currentCline.clineMessages.findIndex((msg: ClineMessage) => msg.ts === messageTs)
 		const apiConversationHistoryIndex = currentCline.apiConversationHistory.findIndex(
-			(msg: ApiMessage) => msg.ts && msg.ts >= timeCutoff,
+			(msg: ApiMessage) => msg.ts === messageTs,
 		)
 		return { messageIndex, apiConversationHistoryIndex }
 	}
@@ -165,17 +166,53 @@ export const webviewMessageHandler = async (
 								ts: targetMessage.ts!,
 								commitHash: targetMessage.checkpoint.hash as string,
 								mode: "restore",
+								operation: "delete",
+							})
+
+							// Save the updated messages to disk after checkpoint restoration
+							// This ensures the deleted messages are persisted before reinitialization
+							await saveTaskMessages({
+								messages: currentCline.clineMessages,
+								taskId: currentCline.taskId,
+								globalStoragePath: provider.contextProxy.globalStorageUri.fsPath,
 							})
 						}
+					} else {
+						// For non-checkpoint deletes, preserve checkpoint associations for remaining messages
+						// Store checkpoints from messages that will be preserved
+						const preservedCheckpoints = new Map<number, any>()
+						for (let i = 0; i < messageIndex; i++) {
+							const msg = currentCline.clineMessages[i]
+							if (msg?.checkpoint && msg.ts) {
+								preservedCheckpoints.set(msg.ts, msg.checkpoint)
+							}
+						}
+
+						// Delete this message and all subsequent messages
+						await removeMessagesThisAndSubsequent(currentCline, messageIndex, apiConversationHistoryIndex)
+
+						// Restore checkpoint associations for preserved messages
+						for (const [ts, checkpoint] of preservedCheckpoints) {
+							const msgIndex = currentCline.clineMessages.findIndex((msg) => msg.ts === ts)
+							if (msgIndex !== -1) {
+								currentCline.clineMessages[msgIndex].checkpoint = checkpoint
+							}
+						}
+
+						// Save the updated messages with restored checkpoints
+						await saveTaskMessages({
+							messages: currentCline.clineMessages,
+							taskId: currentCline.taskId,
+							globalStoragePath: provider.contextProxy.globalStorageUri.fsPath,
+						})
 					}
 
 					const { historyItem } = await provider.getTaskWithId(currentCline.taskId)
 
-					// Delete this message and all subsequent messages
-					await removeMessagesThisAndSubsequent(currentCline, messageIndex, apiConversationHistoryIndex)
-
-					// Initialize with history item after deletion
-					await provider.initClineWithHistoryItem(historyItem)
+					// Initialize with history item after deletion (only for checkpoint restores)
+					if (restoreCheckpoint) {
+						await provider.initClineWithHistoryItem(historyItem)
+					}
 				} catch (error) {
 					console.error("Error in delete message:", error)
 					vscode.window.showErrorMessage(
@@ -264,27 +301,79 @@ export const webviewMessageHandler = async (
 
 			if (messageIndex !== -1) {
 				try {
+					const targetMessage = currentCline.clineMessages[messageIndex]
+
+					// Preserve the original checkpoint data for the edited message
+					const originalCheckpoint = targetMessage?.checkpoint
+
 					// If checkpoint restoration is requested, restore to the checkpoint first
 					if (restoreCheckpoint) {
-						const targetMessage = currentCline.clineMessages[messageIndex]
 						if (
-							targetMessage?.checkpoint &&
-							typeof targetMessage.checkpoint === "object" &&
-							"hash" in targetMessage.checkpoint
+							originalCheckpoint &&
+							typeof originalCheckpoint === "object" &&
+							"hash" in originalCheckpoint
 						) {
+							// Store the edited content and images for after restoration
+							const editData = { text: editedContent, images }
+
+							// Set a flag on the provider to indicate we need to process an edit after restoration
+							;(provider as any).pendingEditAfterRestore = {
+								messageTs,
+								editedContent,
+								images,
+								messageIndex,
+								apiConversationHistoryIndex,
+								originalCheckpoint, // Preserve the checkpoint for the new message
+							}
+
 							await currentCline.checkpointRestore({
 								ts: targetMessage.ts!,
-								commitHash: targetMessage.checkpoint.hash as string,
+								commitHash: originalCheckpoint.hash as string,
 								mode: "restore",
+								operation: "edit",
 							})
+
+							// The task will be cancelled and reinitialized by checkpointRestore
+							// The pending edit will be processed in the reinitialized task
+							return
+						}
+					}
+
+					// For non-checkpoint edits, preserve checkpoint associations for remaining messages
+					// Store checkpoints from messages that will be preserved
+					const preservedCheckpoints = new Map<number, any>()
+					for (let i = 0; i < messageIndex; i++) {
+						const msg = currentCline.clineMessages[i]
+						if (msg?.checkpoint && msg.ts) {
+							preservedCheckpoints.set(msg.ts, msg.checkpoint)
 						}
 					}
 
 					// Edit this message and delete subsequent
 					await removeMessagesThisAndSubsequent(currentCline, messageIndex, apiConversationHistoryIndex)
 
+					// Restore checkpoint associations for preserved messages
+					for (const [ts, checkpoint] of preservedCheckpoints) {
+						const msgIndex = currentCline.clineMessages.findIndex((msg) => msg.ts === ts)
+						if (msgIndex !== -1) {
+							currentCline.clineMessages[msgIndex].checkpoint = checkpoint
+						}
+					}
+
+					// Save the updated messages with restored checkpoints
+					await saveTaskMessages({
+						messages: currentCline.clineMessages,
+						taskId: currentCline.taskId,
+						globalStoragePath: provider.contextProxy.globalStorageUri.fsPath,
+					})
+
 					// Process the edited message as a regular user message
-					// This will add it to the conversation and trigger an AI response
+					// Preserve the original checkpoint for the new message
+					if (originalCheckpoint) {
+						// Store the checkpoint to be attached to the new message
+						currentCline.pendingUserMessageCheckpoint = originalCheckpoint
+					}
+
 					webviewMessageHandler(provider, {
 						type: "askResponse",
 						askResponse: "messageResponse",
@@ -457,7 +546,33 @@ export const webviewMessageHandler = async (
 			await provider.postStateToWebview()
 			break
 		case "askResponse":
-			provider.getCurrentCline()?.handleWebviewAskResponse(message.askResponse!, message.text, message.images)
+			// Save checkpoint BEFORE processing the user message if checkpoints are enabled
+			const currentCline = provider.getCurrentCline()
+			if (currentCline && currentCline.enableCheckpoints && message.askResponse === "messageResponse") {
+				console.log("[webviewMessageHandler] Saving checkpoint before user message processing")
+				try {
+					const checkpointResult = await currentCline.checkpointSave(true) // Force checkpoint save
+					console.log("[webviewMessageHandler] Checkpoint result:", checkpointResult)
+					if (checkpointResult?.commit) {
+						// Store checkpoint data temporarily to be used when creating the user_feedback message
+						currentCline.pendingUserMessageCheckpoint = {
+							hash: checkpointResult.commit,
+							timestamp: Date.now(),
+							type: "user_message",
+						}
+						console.log(
+							"[webviewMessageHandler] Set pendingUserMessageCheckpoint:",
+							currentCline.pendingUserMessageCheckpoint,
+						)
+					} else {
+						console.log("[webviewMessageHandler] No commit in checkpoint result")
+					}
+				} catch (error) {
+					console.error("[webviewMessageHandler] Failed to save checkpoint before user message:", error)
+				}
+			}
+
+			currentCline?.handleWebviewAskResponse(message.askResponse!, message.text, message.images)
 			break
 		case "autoCondenseContext":
 			await updateGlobalState("autoCondenseContext", message.bool)
diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index e83ec977cb..bd71021305 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -783,7 +783,23 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 	)
 
 	const visibleMessages = useMemo(() => {
+		// First, collect all checkpoint hashes that are associated with user_feedback messages
+		const userMessageCheckpointHashes = new Set<string>()
+		modifiedMessages.forEach((message) => {
+			if (message.say === "user_feedback" && message.checkpoint) {
+				const checkpoint = message.checkpoint as any
+				if (checkpoint.type === "user_message" && checkpoint.hash) {
+					userMessageCheckpointHashes.add(checkpoint.hash)
+				}
+			}
+		})
+
 		const newVisibleMessages = modifiedMessages.filter((message) => {
+			// Filter out checkpoint_saved messages that are associated with user messages
+			if (message.say === "checkpoint_saved" && message.text && userMessageCheckpointHashes.has(message.text)) {
+				return false
+			}
+
 			if (everVisibleMessagesTsRef.current.has(message.ts)) {
 				// If it was ever visible, and it's not one of the types that should always be hidden once processed, keep it.
 				// This helps prevent flickering for messages like 'api_req_retry_delayed' if they are no longer the absolute last.