diff --git a/src/core/webview/ClaudeDevProvider.ts b/src/core/webview/ClaudeDevProvider.ts
index cfa2092..d37056f 100644
--- a/src/core/webview/ClaudeDevProvider.ts
+++ b/src/core/webview/ClaudeDevProvider.ts
@@ -451,7 +451,7 @@ export class ClaudeDevProvider implements vscode.WebviewViewProvider {
 								timeout: 3_000,
 							})
 							await this.initClaudeDevWithHistoryItem(historyItem) // clears task again, so we need to abortTask manually above
-							await this.postStateToWebview()
+							// await this.postStateToWebview() // new claude dev instance will post state when it's ready. having this here sent an empty messages array to webview leading to virtuoso having to reload the entire list
 						}
 
 						break
diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index 9bac29e..c9c208a 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -55,6 +55,7 @@ const ChatView = ({ isHidden, showAnnouncement, hideAnnouncement, showHistoryVie
 	const [didScrollUp, setDidScrollUp] = useState(false)
 	const lastScrollTopRef = useRef(0)
 	const [didClickScrollToBottom, setDidClickScrollToBottom] = useState(false)
+	const [didClickCancel, setDidClickCancel] = useState(false)
 
 	useEffect(() => {
 		// if last message is an ask, show user ask UI
@@ -134,6 +135,7 @@ const ChatView = ({ isHidden, showAnnouncement, hideAnnouncement, showHistoryVie
 							setEnableButtons(true)
 							setPrimaryButtonText("Resume Task")
 							setSecondaryButtonText(undefined)
+							setDidClickCancel(false) // special case where we reset the cancel button state
 							break
 						case "resume_completed_task":
 							setTextAreaDisabled(false)
@@ -141,6 +143,7 @@ const ChatView = ({ isHidden, showAnnouncement, hideAnnouncement, showHistoryVie
 							setEnableButtons(true)
 							setPrimaryButtonText("Start New Task")
 							setSecondaryButtonText(undefined)
+							setDidClickCancel(false)
 							break
 					}
 					break
@@ -283,6 +286,7 @@ const ChatView = ({ isHidden, showAnnouncement, hideAnnouncement, showHistoryVie
 	const handleSecondaryButtonClick = useCallback(() => {
 		if (isStreaming) {
 			vscode.postMessage({ type: "cancelTask" })
+			setDidClickCancel(true)
 			return
 		}
 
@@ -653,7 +657,7 @@ const ChatView = ({ isHidden, showAnnouncement, hideAnnouncement, showHistoryVie
 							style={{
 								opacity:
 									primaryButtonText || secondaryButtonText || isStreaming
-										? enableButtons || isStreaming
+										? enableButtons || (isStreaming && !didClickCancel)
 											? 1
 											: 0.5
 										: 0,
@@ -675,7 +679,7 @@ const ChatView = ({ isHidden, showAnnouncement, hideAnnouncement, showHistoryVie
 							{(secondaryButtonText || isStreaming) && (
 								<VSCodeButton
 									appearance="secondary"
-									disabled={!enableButtons && !isStreaming}
+									disabled={!enableButtons && !(isStreaming && !didClickCancel)}
 									style={{
 										flex: isStreaming ? 2 : 1,
 										marginLeft: isStreaming ? 0 : "6px",