diff --git a/src/App.css b/src/App.css
index 3c0907a..927a4a0 100644
--- a/src/App.css
+++ b/src/App.css
@@ -627,6 +627,46 @@ body {
   position: relative;
 }
 
+.message-item.grouped {
+  padding-top: 4px;
+  padding-bottom: 4px;
+}
+
+.message-item.grouped .message-header {
+  display: none;
+}
+
+.message-avatar-placeholder {
+  width: 40px;
+  height: 20px; /* Match approximate line-height */
+  flex-shrink: 0;
+  position: relative;
+  display: flex;
+  justify-content: center;
+}
+
+.thread-message-item .message-avatar-placeholder {
+  width: 32px;
+}
+
+.message-hover-timestamp {
+  position: absolute;
+  top: 0;
+  left: 0;
+  width: 100%;
+  text-align: center;
+  font-size: 0.65rem;
+  color: var(--text-muted);
+  opacity: 0;
+  pointer-events: none;
+  line-height: 1.4;
+  padding-top: 2px;
+}
+
+.message-item.grouped:hover .message-hover-timestamp {
+  opacity: 1;
+}
+
 .message-item:hover {
   background-color: rgba(0, 0, 0, 0.05);
 }
diff --git a/src/auth/AuthGate.svelte b/src/auth/AuthGate.svelte
index ac23566..1f7eac6 100644
--- a/src/auth/AuthGate.svelte
+++ b/src/auth/AuthGate.svelte
@@ -99,7 +99,7 @@
             <g class="zep-blimp">
               <!-- Fins / Comic Action Lines -->
               <path d="M15 40 L5 35 M15 50 L2 50 M15 60 L5 65" stroke="currentColor" stroke-width="4" stroke-linecap="round" opacity="0.4" />
-              
+
               <!-- The Chat Bubble Zeppelin Sandwich -->
               <!-- Top Bun -->
               <path d="M25 50 C25 30 45 25 60 25 C85 25 95 35 95 50" class="blimp-top" />
@@ -107,7 +107,7 @@
               <path d="M22 50 C22 50 50 50 98 50" class="blimp-filling" />
               <!-- Bottom Bun + Chat Pointer (Gondola) -->
               <path d="M95 50 C95 65 85 75 60 75 C55 75 50 75 45 85 L38 75 C30 75 25 65 25 50" class="blimp-bottom" />
-              
+
               <!-- Internal "Z" detail -->
               <path d="M55 40 L70 40 L55 60 L70 60" stroke="currentColor" stroke-width="3" fill="none" stroke-linecap="round" opacity="0.3" />
             </g>
diff --git a/src/chat/components/MessageItem.svelte b/src/chat/components/MessageItem.svelte
index d279738..6a8b57c 100644
--- a/src/chat/components/MessageItem.svelte
+++ b/src/chat/components/MessageItem.svelte
@@ -13,11 +13,13 @@
     msg,
     isThread = false,
     isHighlighted = false,
+    isGrouped = false,
     onContentLoad
   }: {
     msg: Types.Message;
     isThread?: boolean;
     isHighlighted?: boolean;
+    isGrouped?: boolean;
     onContentLoad?: () => void;
   } = $props();
 
@@ -145,7 +147,7 @@
 
 <svelte:window onclick={handleGlobalClick} />
 
-<div class="message-item {isHighlighted ? 'active' : ''} {isThread ? 'thread-message-item' : ''}">
+<div class="message-item {isHighlighted ? 'active' : ''} {isThread ? 'thread-message-item' : ''} {isGrouped ? 'grouped' : ''}">
   <div class="message-actions-toolbar">
     {#if chat.isFullyAuthenticated}
       <div class="add-reaction-wrapper" style="position: relative;">
@@ -186,17 +188,25 @@
     {/if}
   </div>
 
-  <!-- svelte-ignore a11y_no_static_element_interactions -->
-  <div oncontextmenu={(e) => {
-    e.preventDefault();
-    e.stopPropagation();
-    const user = chat.users.find(u => u.identity.isEqual(msg.sender));
-    if (user) {
-      chat.userContextMenu = { x: e.clientX, y: e.clientY, user };
-    }
-  }}>
-    <Avatar user={chat.users.find(u => u.identity.isEqual(msg.sender))} size={isThread ? "small" : "medium"} class="message-avatar" />
-  </div>
+  {#if isGrouped}
+    <div class="message-avatar-placeholder">
+      <div class="message-hover-timestamp">
+        {chat.formatTime(msg.sent)}
+      </div>
+    </div>
+  {:else}
+    <!-- svelte-ignore a11y_no_static_element_interactions -->
+    <div oncontextmenu={(e) => {
+      e.preventDefault();
+      e.stopPropagation();
+      const user = chat.users.find(u => u.identity.isEqual(msg.sender));
+      if (user) {
+        chat.userContextMenu = { x: e.clientX, y: e.clientY, user };
+      }
+    }}>
+      <Avatar user={chat.users.find(u => u.identity.isEqual(msg.sender))} size={isThread ? "small" : "medium"} class="message-avatar" />
+    </div>
+  {/if}
 
   <div class="message-content">
     <div class="message-header">
@@ -281,11 +291,11 @@
             {/if}
           {/if}
           <span class="count">{group.length}</span>
-      </button>
-    {/each}
-  </div>
+        </button>
+      {/each}
+    </div>
 
-  {#if !isThread && existingThread}
+    {#if !isThread && existingThread}
       {@const threadMessageCount = chat.allMessages.filter(m => m.threadId === existingThread.id).length}
       <button
         class="thread-link"
@@ -348,4 +358,4 @@
     border: 6px solid transparent;
     border-top-color: var(--background-floating);
   }
-</style>
\ No newline at end of file
+</style>
diff --git a/src/chat/components/MessageList.svelte b/src/chat/components/MessageList.svelte
index 7ffddfd..9a6afff 100644
--- a/src/chat/components/MessageList.svelte
+++ b/src/chat/components/MessageList.svelte
@@ -18,7 +18,7 @@
   function handleScroll() {
     if (!scrollContainer) return;
     const { scrollTop, scrollHeight, clientHeight } = scrollContainer;
-    
+
     // If we are within 100px of the bottom, consider us "at the bottom"
     const atBottom = scrollHeight - scrollTop - clientHeight < 100;
     isAtBottom = atBottom;
@@ -72,7 +72,7 @@
             // If the user is NOT at the bottom, adjust scroll to keep position
             if (!isAtBottom && !isPrepending && !sentByMe) {
               scrollContainer!.scrollTop += heightDiff;
-            } 
+            }
             // If we ARE at the bottom, OR we just sent a message, keep us pinned
             else if (isAtBottom || sentByMe) {
               scrollContainer!.scrollTop = target.scrollHeight;
@@ -100,7 +100,7 @@
   }
 
   $effect(() => {
-    const messages = chat.channelMessages;
+    const messagesLocal = chat.channelMessages;
     const currentChannelId = chat.activeChannelId;
 
     if (isPrepending && scrollContainer) {
@@ -109,13 +109,13 @@
       if (diff > 0) {
         scrollContainer.scrollTop = diff;
         isPrepending = false;
-        lastHeight = newScrollHeight; 
+        lastHeight = newScrollHeight;
       }
     }
 
-    if (messages.length > 0 && scrollContainer) {
+    if (messagesLocal.length > 0 && scrollContainer) {
       const isChannelSwitch = currentChannelId !== lastChannelId;
-      const lastMsg = messages[messages.length - 1];
+      const lastMsg = messagesLocal[messagesLocal.length - 1];
       const myIdHex = chat.identity?.toHexString();
       const lastMsgSenderHex = lastMsg?.sender.toHexString();
       const sentByMe = myIdHex && lastMsgSenderHex && myIdHex === lastMsgSenderHex;
@@ -133,6 +133,27 @@
       }
     }
   });
+
+  const messages = $derived(chat.channelMessages);
+
+  const messageGroups = $derived.by(() => {
+    return messages.map((msg, index) => {
+      if (index === 0) return false;
+      const prevMsg = messages[index - 1];
+
+      try {
+        const sameSender = msg.sender.toHexString() === prevMsg.sender.toHexString();
+        const sameThread = msg.threadId === prevMsg.threadId;
+        const diff = msg.sent.microsSinceUnixEpoch - prevMsg.sent.microsSinceUnixEpoch;
+        // Ensure non-negative and within 5 mins (300,000,000 micros)
+        const withinFiveMinutes = diff >= 0n && diff < 300000000n;
+
+        return sameSender && sameThread && withinFiveMinutes;
+      } catch {
+        return false;
+      }
+    });
+  });
 </script>
 
 <div
@@ -144,11 +165,12 @@
     bind:this={scrollContainer}
     onscroll={handleScroll}
   >
-    {#each chat.channelMessages as msg (msg.id.toString())}
+    {#each messages as msg, i (msg.id.toString())}
       {@const isHighlighted = (chat.pendingThreadParentMessageId === msg.id) || (chat.activeThread?.parentMessageId === msg.id)}
       <MessageItem
         {msg}
         {isHighlighted}
+        isGrouped={messageGroups[i]}
         onContentLoad={handleContentLoad}
       />
     {/each}
diff --git a/src/chat/components/ThreadMessageList.svelte b/src/chat/components/ThreadMessageList.svelte
index b33f2a7..bd444af 100644
--- a/src/chat/components/ThreadMessageList.svelte
+++ b/src/chat/components/ThreadMessageList.svelte
@@ -9,13 +9,35 @@
     threadMessages: readonly Types.Message[],
     onContentLoad?: () => void
   } = $props();
+
+  const messages = $derived(threadMessages);
+
+  const messageGroups = $derived.by(() => {
+    return messages.map((msg, index) => {
+      if (index === 0) return false;
+      const prevMsg = messages[index - 1];
+
+      try {
+        const sameSender = msg.sender.toHexString() === prevMsg.sender.toHexString();
+        const sameThread = msg.threadId === prevMsg.threadId;
+        const diff = msg.sent.microsSinceUnixEpoch - prevMsg.sent.microsSinceUnixEpoch;
+        // Ensure non-negative and within 5 mins (300,000,000 micros)
+        const withinFiveMinutes = diff >= 0n && diff < 300000000n;
+
+        return sameSender && sameThread && withinFiveMinutes;
+      } catch {
+        return false;
+      }
+    });
+  });
 </script>
 
 <div class="thread-messages-inner" style="display: flex; flex-direction: column;">
-  {#each threadMessages as msg (msg.id.toString())}
+  {#each messages as msg, i (msg.id.toString())}
     <MessageItem
       {msg}
       isThread={true}
+      isGrouped={messageGroups[i]}
       {onContentLoad}
     />
   {/each}
diff --git a/src/chat/services/messaging.svelte.ts b/src/chat/services/messaging.svelte.ts
index df8368b..abcc1c0 100644
--- a/src/chat/services/messaging.svelte.ts
+++ b/src/chat/services/messaging.svelte.ts
@@ -171,7 +171,7 @@ export class MessagingService {
     if (!isExpanded) {
       // In non-expanded mode, strictly ONLY show the cache for THIS channel
       return mappedRecent.sort((a, b) =>
-        Number(BigInt(a.sent.microsSinceUnixEpoch) - BigInt(b.sent.microsSinceUnixEpoch))
+        a.sent.microsSinceUnixEpoch < b.sent.microsSinceUnixEpoch ? -1 : (a.sent.microsSinceUnixEpoch > b.sent.microsSinceUnixEpoch ? 1 : 0)
       );
     }
 
@@ -191,7 +191,7 @@ export class MessagingService {
     }
 
     return Array.from(msgMap.values()).sort((a, b) =>
-      Number(BigInt(a.sent.microsSinceUnixEpoch) - BigInt(b.sent.microsSinceUnixEpoch))
+      a.sent.microsSinceUnixEpoch < b.sent.microsSinceUnixEpoch ? -1 : (a.sent.microsSinceUnixEpoch > b.sent.microsSinceUnixEpoch ? 1 : 0)
     );
   }
 
@@ -243,7 +243,7 @@ export class MessagingService {
     }
 
     return Array.from(msgMap.values()).sort((a, b) =>
-      Number(BigInt(a.sent.microsSinceUnixEpoch) - BigInt(b.sent.microsSinceUnixEpoch))
+      a.sent.microsSinceUnixEpoch < b.sent.microsSinceUnixEpoch ? -1 : (a.sent.microsSinceUnixEpoch > b.sent.microsSinceUnixEpoch ? 1 : 0)
     );
   }