diff --git a/main.py b/main.py
index 13dfffd..399714f 100644
--- a/main.py
+++ b/main.py
@@ -209,9 +209,9 @@ def chat_message_watcher(reddit):
     chat_requests_file = os.path.join(DB_DIR, 'chat_wiki_requests.txt')
     processed_message_ids = set()
     subreddit = reddit.subreddit(config.SUBREDDIT)
-    
+
     print("[CHAT] Chat message watcher started")
-    
+
     # Load previously processed message IDs
     if os.path.exists(chat_requests_file):
         try:
@@ -220,14 +220,26 @@ def chat_message_watcher(reddit):
                     processed_message_ids.add(line.strip())
         except Exception as e:
             print(f"[CHAT] Error loading processed message IDs: {e}")
-    
+
+    # Get the latest message timestamp at startup
+    last_seen_timestamp = None
+    try:
+        # Fetch the most recent message (limit=1)
+        latest = list(reddit.inbox.all(limit=1))
+        if latest and hasattr(latest[0], 'created_utc'):
+            last_seen_timestamp = latest[0].created_utc
+            print(f"[CHAT] Last seen message timestamp at startup: {last_seen_timestamp}")
+    except Exception as e:
+        print(f"[CHAT] Error fetching latest message timestamp: {e}")
+
     while True:
         try:
             for message in reddit.inbox.stream():
-                # Skip if no ID or already processed
-                if not hasattr(message, 'id') or message.id in processed_message_ids:
+                # Skip if no ID, already processed, or message is older than startup
+                if (not hasattr(message, 'id') or message.id in processed_message_ids or
+                    (last_seen_timestamp is not None and hasattr(message, 'created_utc') and message.created_utc <= last_seen_timestamp)):
                     continue
-                
+
                 # Mark as processed
                 processed_message_ids.add(message.id)
                 try:
@@ -235,16 +247,16 @@ def chat_message_watcher(reddit):
                         f.write(message.id + '\n')
                 except Exception as e:
                     print(f"[CHAT] Error saving message ID: {e}")
-                
+
                 # Check for reload-config command
                 if hasattr(message, 'body') and 'reload-config' in message.body.lower():
                     author = getattr(message, 'author', None)
-                    
+
                     # Verify sender is a moderator
                     try:
                         if author and author in subreddit.moderator():
                             print(f"[CHAT] Moderator '{author}' requested config reload")
-                            
+
                             # Reload wiki configuration
                             try:
                                 wiki_config.fetch_from_wiki()
@@ -253,18 +265,18 @@ def chat_message_watcher(reddit):
                             except Exception as e:
                                 print(f"[CHAT] Failed to reload wiki config: {e}")
                                 reply_text = f"✗ Failed to reload wiki config: {e}"
-                            
+
                             # Reply to the message
                             try:
                                 message.reply(reply_text)
                                 print(f"[CHAT] Replied to message {message.id}")
                             except Exception as e:
-                                print(f"[CHAT] Error replying to message {message.id}: {e}")
+                                print(f"[CHAT] Error replying to message {message.id}: {message.id}: {e}")
                         else:
                             print(f"[CHAT] Non-moderator '{author}' attempted reload-config (ignored)")
                     except Exception as e:
                         print(f"[CHAT] Error checking moderator status: {e}")
-                
+
                 # Check for repost-latest command
                 elif hasattr(message, 'body') and 'repost-latest' in message.body.lower():
                     author = getattr(message, 'author', None)