diff --git a/apps/web/src/app/(authenticated)/usage/Messages.tsx b/apps/web/src/app/(authenticated)/usage/Messages.tsx
index 07329aff16..ba48eaac5c 100644
--- a/apps/web/src/app/(authenticated)/usage/Messages.tsx
+++ b/apps/web/src/app/(authenticated)/usage/Messages.tsx
@@ -9,6 +9,28 @@ type MessagesProps = {
   messages: Message[];
 };
 
+type QuestionData = {
+  question: string;
+  suggestions: string[];
+};
+
+const parseQuestionData = (text: string): QuestionData | null => {
+  try {
+    const parsed = JSON.parse(text);
+
+    if (parsed?.question && Array.isArray(parsed.suggest)) {
+      return {
+        question: parsed.question,
+        suggestions: parsed.suggest,
+      };
+    }
+  } catch {
+    // Not valid JSON
+  }
+
+  return null;
+};
+
 export const Messages = ({ messages }: MessagesProps) => {
   const conversation = useMemo(
     () =>
@@ -20,31 +42,68 @@ export const Messages = ({ messages }: MessagesProps) => {
 
   return (
     <div className="space-y-6">
-      {conversation.map((message) => (
-        <div
-          key={message.id}
-          className={cn(
-            'flex flex-col gap-3 rounded-lg p-4',
-            message.role === 'user' ? 'bg-primary/10' : 'bg-secondary/10',
-          )}
-        >
-          <div className="flex flex-row items-center justify-between gap-2 text-xs font-medium text-muted-foreground">
-            <div className="flex items-center gap-2">
-              <div>{message.name}</div>
-              <div>&middot;</div>
-              <div>{message.timestamp}</div>
+      {conversation.map((message) => {
+        const isQuestion = message.type === 'ask' && message.ask === 'followup';
+        const isCommand = message.type === 'ask' && message.ask === 'command';
+        const questionData =
+          isQuestion && message.text ? parseQuestionData(message.text) : null;
+
+        return (
+          <div
+            key={message.id}
+            className={cn(
+              'flex flex-col gap-3 rounded-lg p-4',
+              message.role === 'user' ? 'bg-primary/10' : 'bg-secondary/10',
+            )}
+          >
+            <div className="flex flex-row items-center justify-between gap-2 text-xs font-medium text-muted-foreground">
+              <div className="flex items-center gap-2">
+                <div>{message.name}</div>
+                <div>&middot;</div>
+                <div>{message.timestamp}</div>
+              </div>
+              {message.mode && (
+                <div className="px-2 py-1 bg-muted rounded text-xs font-medium">
+                  {message.mode}
+                </div>
+              )}
             </div>
-            {message.mode && (
-              <div className="px-2 py-1 bg-muted rounded text-xs font-medium">
-                {message.mode}
+
+            {isQuestion && questionData ? (
+              <div className="space-y-4">
+                {questionData.question && (
+                  <div className="text-sm leading-relaxed">
+                    {questionData.question}
+                  </div>
+                )}
+                {questionData.suggestions &&
+                  questionData.suggestions.length > 0 && (
+                    <div className="space-y-2">
+                      {questionData.suggestions.map((suggestion, index) => (
+                        <div
+                          key={index}
+                          className="px-4 py-3 bg-background border border-border rounded-md text-sm hover:bg-muted/50 cursor-pointer transition-colors"
+                        >
+                          {suggestion}
+                        </div>
+                      ))}
+                    </div>
+                  )}
+              </div>
+            ) : isCommand ? (
+              <div className="space-y-3">
+                <div className="bg-black/90 text-green-400 p-3 rounded-md font-mono text-sm">
+                  {message.text}
+                </div>
+              </div>
+            ) : (
+              <div className="text-sm leading-relaxed markdown-prose">
+                <ReactMarkdown>{message.text}</ReactMarkdown>
               </div>
             )}
           </div>
-          <div className="text-sm leading-relaxed markdown-prose">
-            <ReactMarkdown>{message.text}</ReactMarkdown>
-          </div>
-        </div>
-      ))}
+        );
+      })}
     </div>
   );
 };
@@ -59,10 +118,22 @@ const decorate = ({ message, index }: { message: Message; index: number }) => {
   return { ...message, role, name, timestamp };
 };
 
-const isVisible = (message: Message) =>
-  (message.ask === 'text' ||
-    message.say === 'text' ||
-    message.say === 'completion_result' ||
-    message.say === 'user_feedback') &&
-  typeof message.text === 'string' &&
-  message.text.length > 0;
+const isVisible = (message: Message) => {
+  // Always show followup and command messages regardless of text content
+  if (
+    message.type === 'ask' &&
+    (message.ask === 'followup' || message.ask === 'command')
+  ) {
+    return true;
+  }
+
+  // For other message types, require non-empty text
+  return (
+    (message.ask === 'text' ||
+      message.say === 'text' ||
+      message.say === 'completion_result' ||
+      message.say === 'user_feedback') &&
+    typeof message.text === 'string' &&
+    message.text.length > 0
+  );
+};