diff --git a/gui/src/components/StepContainer/ResponseActions.tsx b/gui/src/components/StepContainer/ResponseActions.tsx
index 0dc09a438be..ac28afb9dc1 100644
--- a/gui/src/components/StepContainer/ResponseActions.tsx
+++ b/gui/src/components/StepContainer/ResponseActions.tsx
@@ -40,6 +40,7 @@ export default function ResponseActions({
     (state) => state.session.contextPercentage,
   );
   const isPruned = useAppSelector((state) => state.session.isPruned);
+  const historyLength = useAppSelector((state) => state.session.history.length);
   const ruleGenerationSupported = useMemo(() => {
     return selectedModel && modelSupportsNativeTools(selectedModel);
   }, [selectedModel]);
@@ -50,7 +51,7 @@ export default function ResponseActions({
       ? "text-warning"
       : "text-description-muted";
 
-  const showLabel = isLast && (isPruned || percent >= 60);
+  const showLabel = isLast && historyLength >= 4 && (isPruned || percent >= 60);
 
   const compactConversation = useCompactConversation();
 
diff --git a/gui/src/components/mainInput/ContextStatus.tsx b/gui/src/components/mainInput/ContextStatus.tsx
index 63be8f18000..d036c2e2900 100644
--- a/gui/src/components/mainInput/ContextStatus.tsx
+++ b/gui/src/components/mainInput/ContextStatus.tsx
@@ -64,13 +64,17 @@ const ContextStatus = () => {
             {history.length > 0 && (
               <div className="flex flex-col gap-1 whitespace-pre">
                 <div>
-                  <span
-                    className="hover:text-link inline-block cursor-pointer underline"
-                    onClick={() => compactConversation(history.length - 1)}
-                  >
-                    Compact conversation
-                  </span>
-                  {"\n"}
+                  {history.length >= 4 && (
+                    <>
+                      <span
+                        className="hover:text-link inline-block cursor-pointer underline"
+                        onClick={() => compactConversation(history.length - 1)}
+                      >
+                        Compact conversation
+                      </span>
+                      {"\n"}
+                    </>
+                  )}
                   <span
                     className="hover:text-link inline-block cursor-pointer underline"
                     onClick={() => {