diff --git a/src/vs/workbench/contrib/void/browser/chatThreadService.ts b/src/vs/workbench/contrib/void/browser/chatThreadService.ts
index 8df93ec6..9331f841 100644
--- a/src/vs/workbench/contrib/void/browser/chatThreadService.ts
+++ b/src/vs/workbench/contrib/void/browser/chatThreadService.ts
@@ -104,7 +104,7 @@ type ThreadType = {
 
 	// this doesn't need to go in a state object, but feels right
 	state: {
-		latestCheckpointIdx: number | null; // the latest checkpoint we're standing at or null
+		currCheckpointIdx: number | null; // the latest checkpoint we're standing at or null
 
 		stagingSelections: StagingSelectionItem[];
 		focusedMessageIdx: number | undefined; // index of the user message that is being edited (undefined if none)
@@ -122,7 +122,7 @@ type ChatThreads = {
 }
 
 export const defaultThreadState: ThreadType['state'] = {
-	latestCheckpointIdx: null,
+	currCheckpointIdx: null,
 	stagingSelections: [],
 	focusedMessageIdx: undefined,
 	linksOfMessageIdx: {},
@@ -629,8 +629,6 @@ class ChatThreadService extends Disposable implements IChatThreadService {
 					delete this._currentlyRunningToolInterruptor[threadId];
 				}
 				toolResult = await result // ts is bad... await is needed
-
-				if (toolName === 'edit') { this._addOrUpdateToolEditCheckpoint({ threadId, uri: (toolParams as ToolCallParams['edit']).uri }) }
 			}
 			catch (error) {
 				if (interrupted) {
@@ -654,6 +652,9 @@ class ChatThreadService extends Disposable implements IChatThreadService {
 
 			// 5. add to history and keep going
 			this._addMessageToThread(threadId, { role: 'tool', name: toolName, paramsStr: toolParamsStr, id: toolId, content: toolResultStr, result: { type: 'success', params: toolParams, value: toolResult }, })
+
+			// 6. add a checkpoint
+			if (toolName === 'edit') { this._addToolEditCheckpoint({ threadId, uri: (toolParams as ToolCallParams['edit']).uri }) }
 			return {}
 		};
 
@@ -778,35 +779,41 @@ class ChatThreadService extends Disposable implements IChatThreadService {
 		const newThread = this.state.allThreads[threadId]
 		if (!newThread) return // should never happen
 		const latestCheckpointIdx = newThread.messages.length - 1
-		this._setThreadState(threadId, { latestCheckpointIdx })
+		this._setThreadState(threadId, { currCheckpointIdx: latestCheckpointIdx })
 	}
 
 	// merge any LLM checkpoint before this one (and after a user checkpoint if one exists), and add the checkpoint
 	// call this right after LLM edits a file
-	private _addOrUpdateToolEditCheckpoint({ threadId, uri, }: { threadId: string, uri: URI }) {
+	private _addToolEditCheckpoint({ threadId, uri, }: { threadId: string, uri: URI }) {
 		const thread = this.state.allThreads[threadId]
 		if (!thread) return
 		const { model } = this._voidModelService.getModel(uri)
 		if (!model) return // should never happen
 
-		const lastUserCheckpointIdx = findLastIdx(thread.messages, (m) => m.role === 'checkpoint' && m.type === 'after_user_edits')
-		const prevLLMCheckpointIdx = thread.messages.findIndex((m, i) => i > lastUserCheckpointIdx && m.role === 'checkpoint' && m.type === 'after_tool_edits')
 
 		const afterStr = model.getValue() // afterStr = the value of the file right after the edit
 
-		let prevLLMCheckpoint: LLMCheckpoint | undefined = undefined
-		if (prevLLMCheckpointIdx !== -1) {
-			prevLLMCheckpoint = thread.messages[prevLLMCheckpointIdx] as ChatMessage & { role: 'checkpoint', type: 'after_tool_edits' }
-			this._removeMessageFromThread(threadId, prevLLMCheckpointIdx)
-		}
 		const newLLMCheckpoint: LLMCheckpoint = {
 			role: 'checkpoint',
 			type: 'after_tool_edits',
 			afterStrOfURI: {
-				...prevLLMCheckpoint?.afterStrOfURI,
 				[uri.fsPath]: afterStr,
 			},
 		}
+
+		// remove and merge
+		// const lastUserCheckpointIdx = findLastIdx(thread.messages, (m) => m.role === 'checkpoint' && m.type === 'after_user_edits')
+		// const prevLLMCheckpointIdx = thread.messages.findIndex((m, i) => i > lastUserCheckpointIdx && m.role === 'checkpoint' && m.type === 'after_tool_edits')
+		// let prevLLMCheckpoint: LLMCheckpoint | undefined = undefined
+		// if (prevLLMCheckpointIdx !== -1) {
+		// 	prevLLMCheckpoint = thread.messages[prevLLMCheckpointIdx] as ChatMessage & { role: 'checkpoint', type: 'after_tool_edits' }
+		// 	this._removeMessageFromThread(threadId, prevLLMCheckpointIdx)
+		// 	newLLMCheckpoint.afterStrOfURI = {
+		// 		...newLLMCheckpoint.afterStrOfURI,
+		// 		...prevLLMCheckpoint?.afterStrOfURI,
+		// 	}
+		// }
+
 		this._addCheckpoint(threadId, newLLMCheckpoint)
 
 	}
@@ -894,7 +901,7 @@ class ChatThreadService extends Disposable implements IChatThreadService {
 		const c = this._getCheckpointAfter({ threadId, messageIdx })
 		if (c === undefined) return // should never happen
 
-		const fromIdx = thread.state.latestCheckpointIdx
+		const fromIdx = thread.state.currCheckpointIdx
 		if (fromIdx === null) return // should never happen
 
 		// TODO!!! change toIdx if there's a checkpointModification on the To, and add a checkpoint modification on the from
@@ -990,7 +997,7 @@ We only need to do it for files that were edited since `from`, ie files between
 			}
 		}
 
-		this._setThreadState(threadId, { latestCheckpointIdx: toIdx })
+		this._setThreadState(threadId, { currCheckpointIdx: toIdx })
 		// TODO!!! add/merge a checkpoint modification if relevant
 	}
 
diff --git a/src/vs/workbench/contrib/void/browser/react/src/sidebar-tsx/SidebarChat.tsx b/src/vs/workbench/contrib/void/browser/react/src/sidebar-tsx/SidebarChat.tsx
index 7e948af7..beba18f1 100644
--- a/src/vs/workbench/contrib/void/browser/react/src/sidebar-tsx/SidebarChat.tsx
+++ b/src/vs/workbench/contrib/void/browser/react/src/sidebar-tsx/SidebarChat.tsx
@@ -25,7 +25,7 @@ import { VOID_OPEN_SETTINGS_ACTION_ID } from '../../../voidSettingsPane.js';
 import { ChatMode, FeatureName, isFeatureNameDisabled } from '../../../../../../../workbench/contrib/void/common/voidSettingsTypes.js';
 import { WarningBox } from '../void-settings-tsx/WarningBox.js';
 import { getModelCapabilities, getIsResoningEnabledState } from '../../../../common/modelCapabilities.js';
-import { AlertTriangle, Ban, ChevronRight, Dot, Pencil, X } from 'lucide-react';
+import { AlertTriangle, Ban, ChevronRight, Dot, Pencil, Undo, Undo2, X } from 'lucide-react';
 import { ChatMessage, StagingSelectionItem, ToolMessage, ToolRequestApproval } from '../../../../common/chatThreadServiceTypes.js';
 import { ToolCallParams, ToolName, toolNames, ToolNameWithApproval } from '../../../../common/toolsServiceTypes.js';
 import { ApplyButtonsHTML, CopyButton, JumpToFileButton, JumpToTerminalButton, StatusIndicatorHTML, useApplyButtonState } from '../markdown/ApplyBlockHoverButtons.js';
@@ -988,7 +988,7 @@ const UserMessageComponent = ({ chatMessage, messageIdx, isCommitted, _scrollToB
 		</div>
 
 
-		{<EditSymbol
+		<EditSymbol
 			size={18}
 			className={`
 				absolute -top-1 -right-1
@@ -1006,7 +1006,7 @@ const UserMessageComponent = ({ chatMessage, messageIdx, isCommitted, _scrollToB
 					onCloseEdit()
 				}
 			}}
-		/>}
+		/>
 
 	</div>
 
@@ -1821,12 +1821,18 @@ const toolNameToComponent: { [T in ToolName]: ToolComponent<T> } = {
 const Checkpoint = ({ threadId, messageIdx }: { threadId: string; messageIdx: number }) => {
 	const accessor = useAccessor()
 	const chatThreadService = accessor.get('IChatThreadService')
-
-	return <button onClick={() => {
-		chatThreadService.jumpToCheckpointAfterMessageIdx({ threadId, messageIdx })
-	}}>
-		jump
-	</button>
+	const commandBarService = accessor.get('IVoidCommandBarService')
+	return <div
+		className='pointer-events-auto cursor-pointer select-none hover:brightness-125 flex items-center justify-center'
+		onClick={() => {
+			// reject all current changes and then jump back
+			commandBarService.acceptOrRejectAllFiles({ behavior: 'reject' })
+			chatThreadService.jumpToCheckpointAfterMessageIdx({ threadId, messageIdx })
+		}}>
+		<div className='bg-void-border-1 h-[1px] flex-grow'></div>
+		<div className='px-2'>Checkpoint</div>
+		<div className='bg-void-border-1 h-[1px] flex-grow'></div>
+	</div>
 
 }
 
@@ -2021,18 +2027,22 @@ export const SidebarChat = () => {
 
 	const previousMessagesHTML = useMemo(() => {
 		const threadId = currentThread.id
+		const currCheckpointIdx = chatThreadsState.allThreads[threadId]?.state?.currCheckpointIdx ?? Infinity // if not exist, treat like checkpoint is last message (infinity)
+
 		return previousMessages.map((message, i) => {
 			const isLast = i === numMessages - 1 && (isRunning === 'tool' || isRunning === 'awaiting_user')
-			return <ChatBubble key={getChatBubbleId(currentThread.id, i)}
-				chatMessage={message}
-				messageIdx={i}
-				isCommitted={true}
-				chatIsRunning={isRunning}
-				isLast={isLast}
-				threadId={threadId}
-				isToolBeingWritten={toolIsLoading}
-				_scrollToBottom={() => scrollToBottom(scrollContainerRef)}
-			/>
+			return <div className={`${currCheckpointIdx < i ? 'opacity-50 pointer-events-none select-none' : ''}`}>
+				<ChatBubble key={getChatBubbleId(currentThread.id, i)}
+					chatMessage={message}
+					messageIdx={i}
+					isCommitted={true}
+					chatIsRunning={isRunning}
+					isLast={isLast}
+					threadId={threadId}
+					isToolBeingWritten={toolIsLoading}
+					_scrollToBottom={() => scrollToBottom(scrollContainerRef)}
+				/>
+			</div>
 		})
 	}, [previousMessages, isRunning, currentThread, numMessages])