diff --git a/frontend/dashboard/src/components/conversation/MessageBubble.tsx b/frontend/dashboard/src/components/conversation/MessageBubble.tsx
index 228cf76..01894ec 100644
--- a/frontend/dashboard/src/components/conversation/MessageBubble.tsx
+++ b/frontend/dashboard/src/components/conversation/MessageBubble.tsx
@@ -92,15 +92,13 @@ export default function MessageBubble({
 
 function UserBubble({ message }: { message: ConversationMessage }) {
   const [showWrapper, setShowWrapper] = useState(false);
-  const hasWrapper = SYSTEM_REMINDER_PATTERN.test(message.text);
   let displayText = message.text;
   let wrapperText = "";
-  if (hasWrapper) {
-    const m = message.text.match(/^([\s\S]*?<\/(system-reminder|command-name|local-command-stdout|command-message|command-args)>\s*)/i);
-    if (m) {
-      wrapperText = m[1];
-      displayText = message.text.slice(m[1].length);
-    }
+  while (SYSTEM_REMINDER_PATTERN.test(displayText)) {
+    const m = displayText.match(/^([\s\S]*?<\/(system-reminder|command-name|local-command-stdout|command-message|command-args)>\s*)/i);
+    if (!m) break;
+    wrapperText += m[1];
+    displayText = displayText.slice(m[1].length);
   }
 
   return (
diff --git a/frontend/dashboard/src/components/conversation/TerminalView.tsx b/frontend/dashboard/src/components/conversation/TerminalView.tsx
index dbce905..9f50558 100644
--- a/frontend/dashboard/src/components/conversation/TerminalView.tsx
+++ b/frontend/dashboard/src/components/conversation/TerminalView.tsx
@@ -88,17 +88,15 @@ function ContinuationRow({ children }: { children: ReactNode }) {
 
 function UserRow({ message }: { message: ConversationMessage }) {
   const [showWrapper, setShowWrapper] = useState(false);
-  const hasWrapper = SYSTEM_REMINDER_PATTERN.test(message.text);
   let displayText = message.text;
   let wrapperText = "";
-  if (hasWrapper) {
-    const m = message.text.match(
+  while (SYSTEM_REMINDER_PATTERN.test(displayText)) {
+    const m = displayText.match(
       /^([\s\S]*?<\/(system-reminder|command-name|local-command-stdout|command-message|command-args)>\s*)/i,
     );
-    if (m) {
-      wrapperText = m[1];
-      displayText = message.text.slice(m[1].length);
-    }
+    if (!m) break;
+    wrapperText += m[1];
+    displayText = displayText.slice(m[1].length);
   }
   return (
     <div className="mt-4 flex gap-2 rounded-compact bg-n-surface px-2 py-1">