diff --git a/src/frontends/tui/components/App.tsx b/src/frontends/tui/components/App.tsx
index 5e67298..9b8068e 100644
--- a/src/frontends/tui/components/App.tsx
+++ b/src/frontends/tui/components/App.tsx
@@ -78,10 +78,19 @@ export function App({
   onTransfer,
   onExit,
 }: AppProps): React.ReactElement {
+  const ensureTimestamp = useCallback((message: Message): Message => ({
+    ...message,
+    timestamp: message.timestamp ?? Date.now(),
+  }), []);
+
+  const ensureTimestamps = useCallback((history: Message[]): Message[] => (
+    history.map(ensureTimestamp)
+  ), [ensureTimestamp]);
+
   const ctrlCExitWindowMs = 1_500;
   const { exit } = useApp();
   const [input, setInput] = useState('');
-  const [messages, setMessages] = useState<Message[]>(session.getHistory());
+  const [messages, setMessages] = useState<Message[]>(ensureTimestamps(session.getHistory()));
   const [isStreaming, setIsStreaming] = useState(false);
   const [streamingContent, setStreamingContent] = useState('');
   const [scrollOffset, setScrollOffset] = useState(0);
@@ -682,7 +691,7 @@ export function App({
       const messageWithTimestamp = session.addMessage(userMessage);
       setMessages(prev => [...prev, messageWithTimestamp]);
     } else {
-      setMessages(prev => [...prev, { ...userMessage, timestamp: Date.now() }]);
+      setMessages(prev => [...prev, ensureTimestamp(userMessage)]);
     }
     setScrollOffset(0);
 
@@ -696,7 +705,7 @@ export function App({
         await agent.process(command.content);
         const usage = agent.getUsage();
         setTokenUsage({ inputTokens: usage.inputTokens, outputTokens: usage.outputTokens });
-        setMessages(session.getHistory());
+        setMessages(ensureTimestamps(session.getHistory()));
       } else if (modelClient.chatStream) {
         let fullContent = '';
 
@@ -757,6 +766,8 @@ export function App({
     exit,
     onExit,
     isStreaming,
+    ensureTimestamp,
+    ensureTimestamps,
     messages.length,
     tokenUsage.inputTokens,
     tokenUsage.outputTokens,
diff --git a/src/frontends/tui/components/MessageList.tsx b/src/frontends/tui/components/MessageList.tsx
index b7d311f..66fa002 100644
--- a/src/frontends/tui/components/MessageList.tsx
+++ b/src/frontends/tui/components/MessageList.tsx
@@ -13,16 +13,12 @@ export interface MessageListProps {
 }
 
 // Helper to format timestamp in human-readable way
-function formatTimestamp(timestamp: number): string {
+function formatTimestampParts(timestamp: number): { date: string; time: string } {
   const date = new Date(timestamp);
-  const now = new Date();
-  const isSameDay = date.toDateString() === now.toDateString();
-
-  if (isSameDay) {
-    return date.toLocaleTimeString([], { hour: '2-digit', minute: '2-digit' });
-  }
-
-  return date.toLocaleString([], { month: 'short', day: 'numeric', hour: '2-digit', minute: '2-digit' });
+  return {
+    date: date.toLocaleDateString([], { month: 'short', day: 'numeric', year: 'numeric' }),
+    time: date.toLocaleTimeString([], { hour: '2-digit', minute: '2-digit' }),
+  };
 }
 
 // Individual message component
@@ -35,7 +31,7 @@ const MessageItem = memo(function MessageItem({
 }): React.ReactElement {
   const isUser = message.role === 'user';
   const accentColor = isUser ? 'blue' : '#ff8c00';
-  const timestampText = message.timestamp ? formatTimestamp(message.timestamp) : 'unknown time';
+  const timestamp = formatTimestampParts(message.timestamp ?? Date.now());
 
   return (
     <Box
@@ -55,7 +51,7 @@ const MessageItem = memo(function MessageItem({
           <Text color={accentColor} bold>
             {isUser ? 'You' : 'Flynn'}
           </Text>
-          <Text color="gray">| {timestampText}</Text>
+          <Text color="gray">| {timestamp.date} | {timestamp.time}</Text>
         </Box>
 
         {/* Content */}
diff --git a/src/frontends/tui/minimal.ts b/src/frontends/tui/minimal.ts
index 855c9e9..df8a472 100644
--- a/src/frontends/tui/minimal.ts
+++ b/src/frontends/tui/minimal.ts
@@ -48,12 +48,16 @@ export function formatPrompt(state: 'default' | 'thinking'): string {
   return `${colors.orange}${colors.bold}flynn>${colors.reset} `;
 }
 
-function formatMessageTime(timestamp: number): string {
-  return new Date(timestamp).toLocaleTimeString([], {
-    hour: '2-digit',
-    minute: '2-digit',
-    second: '2-digit',
-  });
+function formatMessageTimestampParts(timestamp: number): { date: string; time: string } {
+  const date = new Date(timestamp);
+  return {
+    date: date.toLocaleDateString([], { month: 'short', day: 'numeric', year: 'numeric' }),
+    time: date.toLocaleTimeString([], {
+      hour: '2-digit',
+      minute: '2-digit',
+      second: '2-digit',
+    }),
+  };
 }
 
 export interface MinimalTuiConfig {
@@ -1237,9 +1241,16 @@ export class MinimalTui {
   }
 
   private async handleMessage(content: string): Promise<void> {
+    const userTimestamp = formatMessageTimestampParts(Date.now());
+    process.stdout.write(
+      `\n${colors.blue}${colors.bold}You${colors.reset} ${colors.gray}[${userTimestamp.date} | ${userTimestamp.time}]${colors.reset}\n`,
+    );
+    process.stdout.write(`${content}\n`);
+
+    const assistantTimestamp = formatMessageTimestampParts(Date.now());
     // Print Flynn label before response
     process.stdout.write(
-      `\n${colors.orange}${colors.bold}Flynn${colors.reset} ${colors.gray}[${formatMessageTime(Date.now())}]${colors.reset}\n`,
+      `\n${colors.orange}${colors.bold}Flynn${colors.reset} ${colors.gray}[${assistantTimestamp.date} | ${assistantTimestamp.time}]${colors.reset}\n`,
     );
     this.startBusyIndicator();