diff --git a/chatserver/server.py b/chatserver/server.py
index 68f5483..e9b68fe 100644
--- a/chatserver/server.py
+++ b/chatserver/server.py
@@ -248,6 +248,50 @@ def get_history():
     # Return the full message history with timestamps
     return jsonify({"messages": message_history[chat_room]})
 
+@app.route('/send_direct_message', methods=['POST'])
+def send_direct_message():
+    """Send a direct message to a specific user."""
+    data = request.json
+    sender_username = data.get('sender_username')
+    target_username = data.get('target_username')
+    message = data.get('message')
+
+    if not sender_username or not target_username or not message:
+        return jsonify({"error": "Sender username, target username, and message are required"}), 400
+
+    timestamp = datetime.now().strftime('%Y-%m-%d %H:%M:%S')
+
+    # Check if the target is a socket-based client
+    target_sock = None
+    for s, info in client_info.items():
+        if not info.get("is_websocket") and info.get("username") == target_username:
+            target_sock = s
+            break
+
+    # Check if the target is a WebSocket client
+    target_websocket_sid = None
+    for sid, info in client_info.items():
+        if info.get("is_websocket") and info.get("username") == target_username:
+            target_websocket_sid = sid
+            break
+
+    if target_sock:
+        # Send the direct message to the socket-based client
+        target_sock.send(f"[{timestamp}] DM from {sender_username}: {message}\n".encode('utf-8'))
+        return jsonify({"status": "Direct message sent to socket-based client"}), 200
+    elif target_websocket_sid:
+        # Send the direct message to the WebSocket client
+        socketio.emit('message', {
+            'username': sender_username,
+            'message': message,
+            'timestamp': timestamp,
+            'chat_room': 'Direct Message'
+        }, to=target_websocket_sid)
+        return jsonify({"status": "Direct message sent to WebSocket client"}), 200
+    else:
+        # Target user not found
+        return jsonify({"error": "Target user not found"}), 404
+
 # WebSocket event handlers
 @socketio.on('connect')
 def handle_connect():