diff --git a/ui/colony/src/App.tsx b/ui/colony/src/App.tsx
index 77779f4..8a1685b 100644
--- a/ui/colony/src/App.tsx
+++ b/ui/colony/src/App.tsx
@@ -210,10 +210,12 @@ export default function App() {
               const prev = i > 0 ? messages[i - 1] : null;
               const sameSender = prev && prev.user.username === msg.user.username;
               const withinWindow = prev && (new Date(msg.created_at).getTime() - new Date(prev.created_at).getTime()) < 5 * 60 * 1000;
-              const compact = !!(sameSender && withinWindow && !msg.reply_to);
               const prevDate = prev ? new Date(prev.created_at).toDateString() : null;
               const thisDate = new Date(msg.created_at).toDateString();
               const showDate = prevDate !== thisDate;
+              // Don't compact: after date break, typed messages (non-text), or replies
+              const isTyped = msg.type !== "text";
+              const compact = !!(sameSender && withinWindow && !msg.reply_to && !showDate && !isTyped);
 
               return (
                 <div key={msg.id}>
diff --git a/ui/colony/src/components/MessageItem.tsx b/ui/colony/src/components/MessageItem.tsx
index 96ab5a6..f34e5b1 100644
--- a/ui/colony/src/components/MessageItem.tsx
+++ b/ui/colony/src/components/MessageItem.tsx
@@ -35,7 +35,8 @@ function timeAgo(dateStr: string): string {
 
 function renderContent(text: string) {
   // Split on @mentions and URLs
-  const parts = text.split(/((?:https?:\/\/)[^\s]+|@[\w-]+)/g);
+  // URL regex: stop before trailing punctuation like ),. etc
+  const parts = text.split(/((?:https?:\/\/)[^\s),.\]}>]+|@[\w-]+)/g);
   return parts.map((part, i) => {
     if (part.startsWith("@")) {
       return (