diff --git a/monkey/infection_monkey/monkey.py b/monkey/infection_monkey/monkey.py
index 73468a3c419..5a0ba093857 100644
--- a/monkey/infection_monkey/monkey.py
+++ b/monkey/infection_monkey/monkey.py
@@ -9,7 +9,6 @@
 
 from pubsub.core import Publisher
 
-import infection_monkey.tunnel as tunnel
 from common.event_queue import IEventQueue, PyPubSubEventQueue
 from common.events import CredentialsStolenEvent
 from common.network.network_utils import address_to_ip_port
@@ -45,6 +44,7 @@
 from infection_monkey.network.relay import TCPRelay
 from infection_monkey.network.relay.utils import (
     find_server,
+    notify_disconnect,
     send_remove_from_waitlist_control_message_to_relays,
 )
 from infection_monkey.network_scanning.elasticsearch_fingerprinter import ElasticSearchFingerprinter
@@ -415,21 +415,18 @@ def cleanup(self):
             ).send()  # Signal the server (before closing the tunnel)
 
             self._close_tunnel()
-            self._singleton.unlock()
         except Exception as e:
             logger.error(f"An error occurred while cleaning up the monkey agent: {e}")
             if deleted is None:
                 InfectionMonkey._self_delete()
+        finally:
+            self._singleton.unlock()
 
         logger.info("Monkey is shutting down")
 
     def _close_tunnel(self):
-        tunnel_address = (
-            self._control_client.proxies.get("https", "").replace("http://", "").split(":")[0]
-        )
-        if tunnel_address:
-            logger.info("Quitting tunnel %s", tunnel_address)
-            tunnel.quit_tunnel(tunnel_address)
+        logger.info(f"Quitting tunnel {self._cmd_island_ip}")
+        notify_disconnect(self._cmd_island_ip, self._cmd_island_port)
 
     def _send_log(self):
         monkey_log_path = get_agent_log_path()
diff --git a/monkey/infection_monkey/network/relay/__init__.py b/monkey/infection_monkey/network/relay/__init__.py
index b9eb8a009d1..50ee9643899 100644
--- a/monkey/infection_monkey/network/relay/__init__.py
+++ b/monkey/infection_monkey/network/relay/__init__.py
@@ -7,3 +7,4 @@
 from .tcp_connection_handler import TCPConnectionHandler
 from .tcp_pipe_spawner import TCPPipeSpawner
 from .tcp_relay import TCPRelay
+from .utils import notify_disconnect
diff --git a/monkey/infection_monkey/network/relay/utils.py b/monkey/infection_monkey/network/relay/utils.py
index 096500c5bdb..7ab38581b31 100644
--- a/monkey/infection_monkey/network/relay/utils.py
+++ b/monkey/infection_monkey/network/relay/utils.py
@@ -1,5 +1,6 @@
 import logging
 import socket
+from ipaddress import IPv4Address
 from typing import Iterable, Optional
 
 import requests
@@ -49,14 +50,21 @@ def send_remove_from_waitlist_control_message_to_relays(servers: Iterable[str]):
 
 
 def _send_remove_from_waitlist_control_message_to_relay(server: str):
-    with socket.socket(socket.AF_INET, socket.SOCK_STREAM) as d_socket:
-        d_socket.settimeout(MEDIUM_REQUEST_TIMEOUT)
+    ip, port = address_to_ip_port(server)
+    notify_disconnect(IPv4Address(ip), int(port))
+
 
-        ip, port = address_to_ip_port(server)
-        logger.info(f"Control message was sent to the server/relay {server}")
+def notify_disconnect(server_ip: IPv4Address, server_port: int):
+    """
+    Tell upstream relay that we no longer need the relay.
 
+    :param server_ip: The IP address of the server to notify.
+    :param server_port: The port of the server to notify.
+    """
+    with socket.socket(socket.AF_INET, socket.SOCK_STREAM) as d_socket:
         try:
-            d_socket.connect((ip, int(port)))
-            d_socket.send(RELAY_CONTROL_MESSAGE_REMOVE_FROM_WAITLIST)
+            d_socket.connect((server_ip, server_port))
+            d_socket.sendall(RELAY_CONTROL_MESSAGE_REMOVE_FROM_WAITLIST)
+            logger.info(f"Control message was sent to the server/relay {server_ip}:{server_port}")
         except OSError as err:
-            logger.error(f"Error connecting to socket {server}: {err}")
+            logger.error(f"Error connecting to socket {server_ip}:{server_port}: {err}")