diff --git a/.changeset/ninety-birds-appear.md b/.changeset/ninety-birds-appear.md
new file mode 100644
index 0000000000..d3740a018a
--- /dev/null
+++ b/.changeset/ninety-birds-appear.md
@@ -0,0 +1,5 @@
+---
+"roo-cline": patch
+---
+
+Fix bug where auto-approval was intermittently failing
diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index de2092248d..38b8997faf 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -240,6 +240,8 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 		if (lastMessage) {
 			switch (lastMessage.type) {
 				case "ask":
+					// Reset user response flag when a new ask arrives to allow auto-approval
+					userRespondedRef.current = false
 					const isPartial = lastMessage.partial === true
 					switch (lastMessage.ask) {
 						case "api_req_failed":