diff --git a/src/judas_server/backend/backend_server.py b/src/judas_server/backend/backend_server.py
index 98f49d4..7bf4f20 100644
--- a/src/judas_server/backend/backend_server.py
+++ b/src/judas_server/backend/backend_server.py
@@ -55,6 +55,8 @@ class BackendServer:
         ] = {}
         self._initialize_handlers()
 
+        self.pending_acks: list[tuple[Client, Message, float]] = []
+
         self.running: bool = False
 
     def _initialize_handlers(self) -> None:
@@ -141,6 +143,22 @@ class BackendServer:
                 )
                 time.sleep(1)
 
+    def send(self, client: Client, msg: Message) -> None:
+        """Send a message to a client.
+
+        Args:
+            client (Client): The client to send the message to.
+            msg (Message): The message to send.
+        """
+        msg_bytes: bytes = msg.to_bytes()
+        self.logger.info(
+            f"[>] Sending message {msg.id} to {client}, category: {msg.category}, action: {msg.action}, ack_required: {msg.ack_required}"
+        )
+        self.logger.debug(f"[>] Message bytes: {msg_bytes!r}")
+        if msg.ack_required:
+            self.pending_acks.append((client, msg, time.time()))
+        client.outbound += msg_bytes
+
     def send_ack(self, client: Client, target_id: str) -> None:
         """Send an ACK message to a client.
 
@@ -148,9 +166,9 @@ class BackendServer:
             client (Client): The client to send the ACK to.
             target_id (str): The id of the ACK'd message.
         """
-        ack: bytes = Message.Control.ack(target_id=target_id).to_bytes()
+        ack: Message = Message.Control.ack(target_id=target_id)
         self.logger.info(f"[>] Sending ACK to {client}")
-        client.outbound += ack
+        self.send(client, ack)
 
     def send_close(self, client: Client) -> None:
         """Send a CLOSE message to a client.
@@ -158,9 +176,9 @@ class BackendServer:
         Args:
             client (Client): The client to send the CLOSE message to.
         """
-        close_msg: bytes = Message.Control.close().to_bytes()
+        close_msg: Message = Message.Control.close()
         self.logger.info(f"[>] Sending CLOSE to {client}")
-        client.outbound += close_msg
+        self.send(client, close_msg)
 
     def _accept_connection(self, sock: socket.socket) -> None:
         """Accept a new client connection.
@@ -335,6 +353,15 @@ class BackendServer:
                         and now - client.last_seen > 60 * 60 * 24  # 24 hours
                     ):
                         self.clients[client.id].status = ClientStatus.STALE
+
+                # check pending ACKs
+                for client, msg, timestamp in self.pending_acks[:]:
+                    if time.time() - timestamp > 5:  # 5 second timeout
+                        self.logger.warning(
+                            f"ACK timeout for message {msg.id} to {client}, resending..."
+                        )
+                        self.send(client, msg)
+                        self.pending_acks.remove((client, msg, timestamp))
                 time.sleep(0.001)  # prevent 100% CPU usage
 
         except Exception as e: