diff --git a/monkey/infection_monkey/network/relay/relay_user_handler.py b/monkey/infection_monkey/network/relay/relay_user_handler.py
index e9ee00d04..2c83f0b13 100644
--- a/monkey/infection_monkey/network/relay/relay_user_handler.py
+++ b/monkey/infection_monkey/network/relay/relay_user_handler.py
@@ -10,6 +10,7 @@ from common.utils.code_utils import del_key
 
 # Wait for potential new clients to connect
 DEFAULT_NEW_CLIENT_TIMEOUT = 2.5 * MEDIUM_REQUEST_TIMEOUT
+DEFAULT_DISCONNECT_TIMEOUT = 60 * 10  # Wait up to 10 minutes for clients to disconnect
 
 
 @dataclass
@@ -21,8 +22,13 @@ class RelayUser:
 class RelayUserHandler:
     """Manages membership to a network relay."""
 
-    def __init__(self, new_client_timeout: float = DEFAULT_NEW_CLIENT_TIMEOUT):
+    def __init__(
+        self,
+        new_client_timeout: float = DEFAULT_NEW_CLIENT_TIMEOUT,
+        client_disconnect_timeout: float = DEFAULT_DISCONNECT_TIMEOUT,
+    ):
         self._new_client_timeout = new_client_timeout
+        self._client_disconnect_timeout = client_disconnect_timeout
         self._relay_users: Dict[IPv4Address, RelayUser] = {}
         self._potential_users: Dict[IPv4Address, RelayUser] = {}
 
@@ -41,6 +47,7 @@ class RelayUserHandler:
                 del_key(self._potential_users, user_address)
 
             timer = EggTimer()
+            timer.set(self._client_disconnect_timeout)
             self._relay_users[user_address] = RelayUser(user_address, timer)
 
     def add_potential_user(self, user_address: IPv4Address):
@@ -74,3 +81,13 @@ class RelayUserHandler:
         )
 
         return len(self._potential_users) > 0
+
+    def has_connected_users(self) -> bool:
+        """
+        Return whether or not we have any relay users.
+        """
+        self._relay_users = dict(
+            filter(lambda ru: not ru[1].timer.is_expired(), self._relay_users.items())
+        )
+
+        return len(self._relay_users) > 0
diff --git a/monkey/infection_monkey/network/relay/tcp_relay.py b/monkey/infection_monkey/network/relay/tcp_relay.py
index a12d8a0d9..f605cdc9d 100644
--- a/monkey/infection_monkey/network/relay/tcp_relay.py
+++ b/monkey/infection_monkey/network/relay/tcp_relay.py
@@ -36,7 +36,7 @@ class TCPRelay(Thread, InterruptableThreadMixin):
         """
         Blocks until the users disconnect or the timeout has elapsed.
         """
-        while self._user_handler.has_potential_users():
+        while self._user_handler.has_potential_users() or self._user_handler.has_connected_users():
             sleep(0.5)
 
     def _wait_for_pipes_to_close(self):
diff --git a/monkey/tests/unit_tests/infection_monkey/network/relay/test_relay_user_handler.py b/monkey/tests/unit_tests/infection_monkey/network/relay/test_relay_user_handler.py
index ca0eb4103..6f3ecb8fa 100644
--- a/monkey/tests/unit_tests/infection_monkey/network/relay/test_relay_user_handler.py
+++ b/monkey/tests/unit_tests/infection_monkey/network/relay/test_relay_user_handler.py
@@ -33,3 +33,18 @@ def test_potential_users_time_out():
     sleep(0.003)
 
     assert not handler.has_potential_users()
+
+
+def test_relay_users_added(handler):
+    assert not handler.has_connected_users()
+    handler.add_relay_user(USER_ADDRESS)
+    assert handler.has_connected_users()
+
+
+def test_relay_users_time_out():
+    handler = RelayUserHandler(client_disconnect_timeout=0.001)
+
+    handler.add_relay_user(USER_ADDRESS)
+    sleep(0.003)
+
+    assert not handler.has_connected_users()