diff --git a/monkey/infection_monkey/monkey.py b/monkey/infection_monkey/monkey.py
index 4ddc8655c..440ab7213 100644
--- a/monkey/infection_monkey/monkey.py
+++ b/monkey/infection_monkey/monkey.py
@@ -110,6 +110,7 @@ class InfectionMonkey:
         # TODO Refactor the telemetry messengers to accept control client
         # and remove control_client_object
         ControlClient.control_client_object = self._control_client
+        self._control_channel = None
         self._telemetry_messenger = LegacyTelemetryMessengerAdapter()
         self._current_depth = self._opts.depth
         self._master = None
@@ -136,6 +137,10 @@ class InfectionMonkey:
             raise Exception(
                 f"Failed to connect to the island via any known servers: {self._opts.servers}"
             )
+
+        # Note: Since we pass the address for each of our interfaces to the exploited
+        # machines, is it possible for a machine to unintentionally unregister itself from the
+        # relay if it is able to connect to the relay over multiple interfaces?
         send_remove_from_waitlist_control_message_to_relays(servers_iterator)
 
         return server
@@ -177,10 +182,10 @@ class InfectionMonkey:
         if firewall.is_enabled():
             firewall.add_firewall_rule()
 
-        control_channel = ControlChannel(self._control_client.server_address, GUID)
-        control_channel.register_agent(self._opts.parent)
+        self._control_channel = ControlChannel(self._control_client.server_address, GUID)
+        self._control_channel.register_agent(self._opts.parent)
 
-        config = control_channel.get_config()
+        config = self._control_channel.get_config()
 
         relay_port = get_free_tcp_port()
         self._relay = TCPRelay(
@@ -204,9 +209,8 @@ class InfectionMonkey:
         local_network_interfaces = InfectionMonkey._get_local_network_interfaces()
 
         # TODO control_channel and control_client have same responsibilities, merge them
-        control_channel = ControlChannel(self._control_client.server_address, GUID)
         propagation_credentials_repository = AggregatingPropagationCredentialsRepository(
-            control_channel
+            self._control_channel
         )
 
         event_queue = PyPubSubAgentEventQueue(Publisher())
@@ -226,7 +230,7 @@ class InfectionMonkey:
             puppet,
             telemetry_messenger,
             victim_host_factory,
-            control_channel,
+            self._control_channel,
             local_network_interfaces,
             propagation_credentials_repository,
         )
@@ -393,10 +397,7 @@ class InfectionMonkey:
                 self._master.cleanup()
 
             reset_signal_handlers()
-
-            if self._relay and self._relay.is_alive():
-                self._relay.stop()
-                self._relay.join(timeout=60)
+            self._stop_relay()
 
             if firewall.is_enabled():
                 firewall.remove_firewall_rule()
@@ -420,6 +421,16 @@ class InfectionMonkey:
 
         logger.info("Monkey is shutting down")
 
+    def _stop_relay(self):
+        if self._relay and self._relay.is_alive():
+            self._relay.stop()
+
+            while self._relay.is_alive() and not self._control_channel.should_agent_stop():
+                self._relay.join(timeout=5)
+
+            if self._control_channel.should_agent_stop():
+                self._relay.join(timeout=60)
+
     def _close_tunnel(self):
         logger.info(f"Quitting tunnel {self._cmd_island_ip}")
         notify_disconnect(self._cmd_island_ip, self._cmd_island_port)
diff --git a/monkey/infection_monkey/network/info.py b/monkey/infection_monkey/network/info.py
index 6fdef3597..6efcf3cd2 100644
--- a/monkey/infection_monkey/network/info.py
+++ b/monkey/infection_monkey/network/info.py
@@ -4,10 +4,12 @@ import struct
 from dataclasses import dataclass
 from ipaddress import IPv4Interface
 from random import shuffle  # noqa: DUO102
-from typing import List
+from threading import Lock
+from typing import Dict, List, Set
 
 import netifaces
 import psutil
+from egg_timer import EggTimer
 
 from infection_monkey.utils.environment import is_windows_os
 
@@ -120,20 +122,93 @@ else:
         return routes
 
 
-def get_free_tcp_port(min_range=1024, max_range=65535):
+class TCPPortSelector:
+    """
+    Select an available TCP port that a new server can listen on
 
-    in_use = {conn.laddr[1] for conn in psutil.net_connections()}
+    Examines the system to find which ports are not in use and makes an intelligent decision
+    regarding what port can be used to host a server. In multithreaded applications, a race occurs
+    between the time when the OS reports that a port is free and when the port is actually used. In
+    other words, two threads which request a free port simultaneously may be handed the same port,
+    as the OS will report that the port is not in use. To combat this, the TCPPortSelector will
+    reserve a port for a period of time to give the requester ample time to start their server. Once
+    the requester's server is listening on the port, the OS will report the port as "LISTEN".
+    """
 
-    for port in COMMON_PORTS:
-        if port not in in_use:
-            return port
+    def __init__(self):
+        self._leases: Dict[int, EggTimer] = {}
+        self._lock = Lock()
 
-    min_range = max(1, min_range)
-    max_range = min(65535, max_range)
-    ports = list(range(min_range, max_range))
-    shuffle(ports)
-    for port in ports:
-        if port not in in_use:
-            return port
+    def get_free_tcp_port(
+        self, min_range: int = 1024, max_range: int = 65535, lease_time_sec: float = 30
+    ):
+        """
+        Get a free TCP port that a new server can listen on
 
-    return None
+        This function will attempt to provide a well-known port that the caller can listen on. If no
+        well-known ports are available, a random port will be selected.
+
+        :param min_range: The smallest port number a random port can be chosen from, defaults to
+                          1024
+        :param max_range: The largest port number a random port can be chosen from, defaults to
+                          65535
+        :param lease_time_sec: The amount of time a port should be reserved for if the OS does not report
+                         it as in use, defaults to 30 seconds
+        :return: A TCP port number
+        """
+        with self._lock:
+            ports_in_use = {conn.laddr[1] for conn in psutil.net_connections()}
+
+            common_port = self._get_free_common_port(ports_in_use, lease_time_sec)
+            if common_port is not None:
+                return common_port
+
+            return self._get_free_random_port(ports_in_use, min_range, max_range, lease_time_sec)
+
+    def _get_free_common_port(self, ports_in_use: Set[int], lease_time_sec):
+        for port in COMMON_PORTS:
+            if self._port_is_available(port, ports_in_use):
+                self._reserve_port(port, lease_time_sec)
+                return port
+
+        return None
+
+    def _get_free_random_port(
+        self, ports_in_use: Set[int], min_range: int, max_range: int, lease_time_sec: float
+    ):
+        min_range = max(1, min_range)
+        max_range = min(65535, max_range)
+        ports = list(range(min_range, max_range))
+        shuffle(ports)
+        for port in ports:
+            if self._port_is_available(port, ports_in_use):
+                self._reserve_port(port, lease_time_sec)
+                return port
+
+        return None
+
+    def _port_is_available(self, port: int, ports_in_use: Set[int]):
+        if port in ports_in_use:
+            return False
+
+        if port not in self._leases:
+            return True
+
+        if self._leases[port].is_expired():
+            return True
+
+        return False
+
+    def _reserve_port(self, port: int, lease_time_sec: float):
+        timer = EggTimer()
+        timer.set(lease_time_sec)
+        self._leases[port] = timer
+
+
+# TODO: This function is here because existing components rely on it. Refactor these components to
+#       accept a TCPPortSelector instance and use that instead.
+def get_free_tcp_port(min_range=1024, max_range=65535, lease_time_sec=30):
+    return get_free_tcp_port.port_selector.get_free_tcp_port(min_range, max_range, lease_time_sec)
+
+
+get_free_tcp_port.port_selector = TCPPortSelector()  # type: ignore[attr-defined]
diff --git a/monkey/infection_monkey/network/relay/consts.py b/monkey/infection_monkey/network/relay/consts.py
new file mode 100644
index 000000000..eb5d3f75a
--- /dev/null
+++ b/monkey/infection_monkey/network/relay/consts.py
@@ -0,0 +1 @@
+SOCKET_TIMEOUT = 10
diff --git a/monkey/infection_monkey/network/relay/relay_connection_handler.py b/monkey/infection_monkey/network/relay/relay_connection_handler.py
index 4b4475e52..91f37b520 100644
--- a/monkey/infection_monkey/network/relay/relay_connection_handler.py
+++ b/monkey/infection_monkey/network/relay/relay_connection_handler.py
@@ -1,11 +1,14 @@
 import socket
 from ipaddress import IPv4Address
+from logging import getLogger
 
 from .relay_user_handler import RelayUserHandler
 from .tcp_pipe_spawner import TCPPipeSpawner
 
 RELAY_CONTROL_MESSAGE_REMOVE_FROM_WAITLIST = b"infection-monkey-relay-control-message: -"
 
+logger = getLogger(__name__)
+
 
 class RelayConnectionHandler:
     """Handles new relay connections."""
@@ -23,10 +26,15 @@ class RelayConnectionHandler:
         addr, _ = sock.getpeername()
         addr = IPv4Address(addr)
 
-        control_message = sock.recv(socket.MSG_PEEK)
+        control_message = sock.recv(
+            len(RELAY_CONTROL_MESSAGE_REMOVE_FROM_WAITLIST), socket.MSG_PEEK
+        )
 
         if control_message.startswith(RELAY_CONTROL_MESSAGE_REMOVE_FROM_WAITLIST):
             self._relay_user_handler.disconnect_user(addr)
         else:
-            self._relay_user_handler.add_relay_user(addr)
-            self._pipe_spawner.spawn_pipe(sock)
+            try:
+                self._pipe_spawner.spawn_pipe(sock)
+                self._relay_user_handler.add_relay_user(addr)
+            except OSError as err:
+                logger.debug(f"Failed to spawn pipe: {err}")
diff --git a/monkey/infection_monkey/network/relay/relay_user_handler.py b/monkey/infection_monkey/network/relay/relay_user_handler.py
index 63c4000e0..390f1d31f 100644
--- a/monkey/infection_monkey/network/relay/relay_user_handler.py
+++ b/monkey/infection_monkey/network/relay/relay_user_handler.py
@@ -1,5 +1,6 @@
 from dataclasses import dataclass
 from ipaddress import IPv4Address
+from logging import getLogger
 from threading import Lock
 from typing import Dict
 
@@ -13,6 +14,9 @@ DEFAULT_NEW_CLIENT_TIMEOUT = 2.5 * MEDIUM_REQUEST_TIMEOUT
 DEFAULT_DISCONNECT_TIMEOUT = 60 * 2  # Wait up to 2 minutes for clients to disconnect
 
 
+logger = getLogger(__name__)
+
+
 @dataclass
 class RelayUser:
     address: IPv4Address
@@ -48,7 +52,9 @@ class RelayUserHandler:
 
             timer = EggTimer()
             timer.set(self._client_disconnect_timeout)
-            self._relay_users[user_address] = RelayUser(user_address, timer)
+            user = RelayUser(user_address, timer)
+            self._relay_users[user_address] = user
+            logger.debug(f"Added relay user {user}")
 
     def add_potential_user(self, user_address: IPv4Address):
         """
@@ -60,7 +66,9 @@ class RelayUserHandler:
         with self._lock:
             timer = EggTimer()
             timer.set(self._new_client_timeout)
-            self._potential_users[user_address] = RelayUser(user_address, timer)
+            user = RelayUser(user_address, timer)
+            self._potential_users[user_address] = user
+            logger.debug(f"Added potential relay user {user}")
 
     def disconnect_user(self, user_address: IPv4Address):
         """
@@ -70,6 +78,7 @@ class RelayUserHandler:
         """
         with self._lock:
             if user_address in self._relay_users:
+                logger.debug(f"Disconnected user {user_address}")
                 del_key(self._relay_users, user_address)
 
     def has_potential_users(self) -> bool:
diff --git a/monkey/infection_monkey/network/relay/sockets_pipe.py b/monkey/infection_monkey/network/relay/sockets_pipe.py
index e31dfaaf4..b4d59416a 100644
--- a/monkey/infection_monkey/network/relay/sockets_pipe.py
+++ b/monkey/infection_monkey/network/relay/sockets_pipe.py
@@ -5,8 +5,9 @@ from logging import getLogger
 from threading import Thread
 from typing import Callable
 
+from .consts import SOCKET_TIMEOUT
+
 READ_BUFFER_SIZE = 8192
-SOCKET_READ_TIMEOUT = 10
 
 logger = getLogger(__name__)
 
@@ -14,25 +15,34 @@ logger = getLogger(__name__)
 class SocketsPipe(Thread):
     """Manages a pipe between two sockets."""
 
+    _thread_count: int = 0
+
     def __init__(
         self,
         source,
         dest,
         pipe_closed: Callable[[SocketsPipe], None],
-        timeout=SOCKET_READ_TIMEOUT,
+        timeout=SOCKET_TIMEOUT,
     ):
         self.source = source
         self.dest = dest
         self.timeout = timeout
-        super().__init__(name=f"SocketsPipeThread-{self.ident}", daemon=True)
+        super().__init__(name=f"SocketsPipeThread-{self._next_thread_num()}", daemon=True)
         self._pipe_closed = pipe_closed
 
+    @classmethod
+    def _next_thread_num(cls):
+        cls._thread_count += 1
+        return cls._thread_count
+
     def _pipe(self):
         sockets = [self.source, self.dest]
-        while True:
+        socket_closed = False
+
+        while not socket_closed:
             read_list, _, except_list = select.select(sockets, [], sockets, self.timeout)
             if except_list:
-                raise Exception("select() failed on sockets {except_list}")
+                raise OSError("select() failed on sockets {except_list}")
 
             if not read_list:
                 raise TimeoutError("pipe did not receive data for {self.timeout} seconds")
@@ -42,21 +52,24 @@ class SocketsPipe(Thread):
                 data = r.recv(READ_BUFFER_SIZE)
                 if data:
                     other.sendall(data)
+                else:
+                    socket_closed = True
+                    break
 
     def run(self):
         try:
             self._pipe()
-        except Exception as err:
+        except OSError as err:
             logger.debug(err)
 
         try:
             self.source.close()
-        except Exception as err:
+        except OSError as err:
             logger.debug(f"Error while closing source socket: {err}")
 
         try:
             self.dest.close()
-        except Exception as err:
+        except OSError as err:
             logger.debug(f"Error while closing destination socket: {err}")
 
         self._pipe_closed(self)
diff --git a/monkey/infection_monkey/network/relay/tcp_connection_handler.py b/monkey/infection_monkey/network/relay/tcp_connection_handler.py
index b70a133bf..f61bc2d3a 100644
--- a/monkey/infection_monkey/network/relay/tcp_connection_handler.py
+++ b/monkey/infection_monkey/network/relay/tcp_connection_handler.py
@@ -1,3 +1,4 @@
+import logging
 import socket
 from threading import Thread
 from typing import Callable, List
@@ -6,6 +7,8 @@ from infection_monkey.utils.threading import InterruptableThreadMixin
 
 PROXY_TIMEOUT = 2.5
 
+logger = logging.getLogger(__name__)
+
 
 class TCPConnectionHandler(Thread, InterruptableThreadMixin):
     """Accepts connections on a TCP socket."""
@@ -24,18 +27,24 @@ class TCPConnectionHandler(Thread, InterruptableThreadMixin):
         InterruptableThreadMixin.__init__(self)
 
     def run(self):
-        l_socket = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
-        l_socket.bind((self.bind_host, self.bind_port))
-        l_socket.settimeout(PROXY_TIMEOUT)
-        l_socket.listen(5)
+        try:
+            l_socket = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
+            l_socket.bind((self.bind_host, self.bind_port))
+            l_socket.settimeout(PROXY_TIMEOUT)
+            l_socket.listen(5)
 
-        while not self._interrupted.is_set():
-            try:
-                source, _ = l_socket.accept()
-            except socket.timeout:
-                continue
+            while not self._interrupted.is_set():
+                try:
+                    source, _ = l_socket.accept()
+                except socket.timeout:
+                    continue
 
-            for notify_client_connected in self._client_connected:
-                notify_client_connected(source)
+                logging.debug(f"New connection received from: {source.getpeername()}")
+                for notify_client_connected in self._client_connected:
+                    notify_client_connected(source)
+        except OSError:
+            logging.exception("Uncaught error in TCPConnectionHandler thread")
+        finally:
+            l_socket.close()
 
-        l_socket.close()
+        logging.info("Exiting connection handler.")
diff --git a/monkey/infection_monkey/network/relay/tcp_pipe_spawner.py b/monkey/infection_monkey/network/relay/tcp_pipe_spawner.py
index 5ffebaaea..0c23f0380 100644
--- a/monkey/infection_monkey/network/relay/tcp_pipe_spawner.py
+++ b/monkey/infection_monkey/network/relay/tcp_pipe_spawner.py
@@ -1,10 +1,14 @@
 import socket
 from ipaddress import IPv4Address
+from logging import getLogger
 from threading import Lock
 from typing import Set
 
+from .consts import SOCKET_TIMEOUT
 from .sockets_pipe import SocketsPipe
 
+logger = getLogger(__name__)
+
 
 class TCPPipeSpawner:
     """
@@ -22,12 +26,13 @@ class TCPPipeSpawner:
         Attempt to create a pipe on between the configured client and the provided socket
 
         :param source: A socket to the connecting client.
-        :raises socket.error: If a socket to the configured client could not be created.
+        :raises OSError: If a socket to the configured client could not be created.
         """
         dest = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
+        dest.settimeout(SOCKET_TIMEOUT)
         try:
-            dest.connect((self._target_addr, self._target_port))
-        except socket.error as err:
+            dest.connect((str(self._target_addr), self._target_port))
+        except OSError as err:
             source.close()
             dest.close()
             raise err
@@ -35,7 +40,8 @@ class TCPPipeSpawner:
         pipe = SocketsPipe(source, dest, self._handle_pipe_closed)
         with self._lock:
             self._pipes.add(pipe)
-        pipe.run()
+
+        pipe.start()
 
     def has_open_pipes(self) -> bool:
         """Return whether or not the TCPPipeSpawner has any open pipes."""
@@ -48,4 +54,5 @@ class TCPPipeSpawner:
 
     def _handle_pipe_closed(self, pipe: SocketsPipe):
         with self._lock:
+            logger.debug(f"Closing pipe {pipe}")
             self._pipes.discard(pipe)
diff --git a/monkey/infection_monkey/network/relay/tcp_relay.py b/monkey/infection_monkey/network/relay/tcp_relay.py
index 8e62a2169..c2663cb1d 100644
--- a/monkey/infection_monkey/network/relay/tcp_relay.py
+++ b/monkey/infection_monkey/network/relay/tcp_relay.py
@@ -1,4 +1,5 @@
 from ipaddress import IPv4Address
+from logging import getLogger
 from threading import Lock, Thread
 from time import sleep
 
@@ -10,6 +11,8 @@ from infection_monkey.network.relay import (
 )
 from infection_monkey.utils.threading import InterruptableThreadMixin
 
+logger = getLogger(__name__)
+
 
 class TCPRelay(Thread, InterruptableThreadMixin):
     """
@@ -23,7 +26,10 @@ class TCPRelay(Thread, InterruptableThreadMixin):
         dest_port: int,
         client_disconnect_timeout: float,
     ):
-        self._user_handler = RelayUserHandler(client_disconnect_timeout=client_disconnect_timeout)
+        self._user_handler = RelayUserHandler(
+            new_client_timeout=client_disconnect_timeout,
+            client_disconnect_timeout=client_disconnect_timeout,
+        )
         self._pipe_spawner = TCPPipeSpawner(dest_addr, dest_port)
         relay_filter = RelayConnectionHandler(self._pipe_spawner, self._user_handler)
         self._connection_handler = TCPConnectionHandler(
@@ -46,6 +52,7 @@ class TCPRelay(Thread, InterruptableThreadMixin):
         self._connection_handler.stop()
         self._connection_handler.join()
         self._wait_for_pipes_to_close()
+        logger.info("TCP Relay closed.")
 
     def add_potential_user(self, user_address: IPv4Address):
         """
diff --git a/monkey/infection_monkey/network/relay/utils.py b/monkey/infection_monkey/network/relay/utils.py
index 4a5532c30..a19f316db 100644
--- a/monkey/infection_monkey/network/relay/utils.py
+++ b/monkey/infection_monkey/network/relay/utils.py
@@ -1,42 +1,75 @@
 import logging
 import socket
+from contextlib import suppress
 from ipaddress import IPv4Address
-from typing import Iterable, Optional
+from typing import Dict, Iterable, Iterator, MutableMapping, Optional
 
 import requests
 
 from common.common_consts.timeouts import MEDIUM_REQUEST_TIMEOUT
 from common.network.network_utils import address_to_ip_port
 from infection_monkey.network.relay import RELAY_CONTROL_MESSAGE_REMOVE_FROM_WAITLIST
-from infection_monkey.utils.threading import create_daemon_thread
+from infection_monkey.utils.threading import (
+    ThreadSafeIterator,
+    create_daemon_thread,
+    run_worker_threads,
+)
 
 logger = logging.getLogger(__name__)
 
+# The number of Island servers to test simultaneously. 32 threads seems large enough for all
+# practical purposes. Revisit this if it's not.
+NUM_FIND_SERVER_WORKERS = 32
+
 
 def find_server(servers: Iterable[str]) -> Optional[str]:
-    for server in servers:
-        logger.debug(f"Trying to connect to server: {server}")
+    server_list = list(servers)
+    server_iterator = ThreadSafeIterator(server_list.__iter__())
+    server_results: Dict[str, bool] = {}
 
-        try:
-            requests.get(  # noqa: DUO123
-                f"https://{server}/api?action=is-up",
-                verify=False,
-                timeout=MEDIUM_REQUEST_TIMEOUT,
-            )
+    run_worker_threads(
+        _find_island_server,
+        "FindIslandServer",
+        args=(server_iterator, server_results),
+        num_workers=NUM_FIND_SERVER_WORKERS,
+    )
 
+    for server in server_list:
+        if server_results[server]:
             return server
-        except requests.exceptions.ConnectionError as err:
-            logger.error(f"Unable to connect to server/relay {server}: {err}")
-        except TimeoutError as err:
-            logger.error(f"Timed out while connecting to server/relay {server}: {err}")
-        except Exception as err:
-            logger.error(
-                f"Exception encountered when trying to connect to server/relay {server}: {err}"
-            )
 
     return None
 
 
+def _find_island_server(servers: Iterator[str], server_status: MutableMapping[str, bool]):
+    with suppress(StopIteration):
+        server = next(servers)
+        server_status[server] = _check_if_island_server(server)
+
+
+def _check_if_island_server(server: str) -> bool:
+    logger.debug(f"Trying to connect to server: {server}")
+
+    try:
+        requests.get(  # noqa: DUO123
+            f"https://{server}/api?action=is-up",
+            verify=False,
+            timeout=MEDIUM_REQUEST_TIMEOUT,
+        )
+
+        return True
+    except requests.exceptions.ConnectionError as err:
+        logger.error(f"Unable to connect to server/relay {server}: {err}")
+    except TimeoutError as err:
+        logger.error(f"Timed out while connecting to server/relay {server}: {err}")
+    except Exception as err:
+        logger.error(
+            f"Exception encountered when trying to connect to server/relay {server}: {err}"
+        )
+
+    return False
+
+
 def send_remove_from_waitlist_control_message_to_relays(servers: Iterable[str]):
     for server in servers:
         t = create_daemon_thread(
diff --git a/monkey/infection_monkey/utils/threading.py b/monkey/infection_monkey/utils/threading.py
index be28aa0b1..6d8b28253 100644
--- a/monkey/infection_monkey/utils/threading.py
+++ b/monkey/infection_monkey/utils/threading.py
@@ -1,8 +1,8 @@
 import logging
 from functools import wraps
 from itertools import count
-from threading import Event, Thread
-from typing import Any, Callable, Iterable, Optional, Tuple
+from threading import Event, Lock, Thread
+from typing import Any, Callable, Iterable, Iterator, Optional, Tuple, TypeVar
 
 logger = logging.getLogger(__name__)
 
@@ -116,3 +116,19 @@ class InterruptableThreadMixin:
     def stop(self):
         """Stop a running thread."""
         self._interrupted.set()
+
+
+T = TypeVar("T")
+
+
+class ThreadSafeIterator(Iterator[T]):
+    """Provides a thread-safe iterator that wraps another iterator"""
+
+    def __init__(self, iterator: Iterator[T]):
+        self._lock = Lock()
+        self._iterator = iterator
+
+    def __next__(self) -> T:
+        while True:
+            with self._lock:
+                return next(self._iterator)
diff --git a/monkey/tests/unit_tests/infection_monkey/network/relay/test_sockets_pipe.py b/monkey/tests/unit_tests/infection_monkey/network/relay/test_sockets_pipe.py
new file mode 100644
index 000000000..0a98c0247
--- /dev/null
+++ b/monkey/tests/unit_tests/infection_monkey/network/relay/test_sockets_pipe.py
@@ -0,0 +1,14 @@
+from unittest.mock import MagicMock
+
+from monkey.infection_monkey.network.relay import SocketsPipe
+
+
+def test_sockets_pipe__name_increments():
+    sock_in = MagicMock()
+    sock_out = MagicMock()
+
+    pipe1 = SocketsPipe(sock_in, sock_out, None)
+    assert pipe1.name.endswith("1")
+
+    pipe2 = SocketsPipe(sock_in, sock_out, None)
+    assert pipe2.name.endswith("2")
diff --git a/monkey/tests/unit_tests/infection_monkey/network/relay/test_utils.py b/monkey/tests/unit_tests/infection_monkey/network/relay/test_utils.py
index 1acd08012..ac7eb1b16 100644
--- a/monkey/tests/unit_tests/infection_monkey/network/relay/test_utils.py
+++ b/monkey/tests/unit_tests/infection_monkey/network/relay/test_utils.py
@@ -20,7 +20,7 @@ servers = [SERVER_1, SERVER_2, SERVER_3, SERVER_4]
         (
             SERVER_2,
             [(SERVER_1, {"exc": requests.exceptions.ConnectionError})]
-            + [(server, {"text": ""}) for server in servers[1:]],
+            + [(server, {"text": ""}) for server in servers[1:]],  # type: ignore[dict-item]
         ),
     ],
 )
@@ -30,3 +30,13 @@ def test_find_server(expected_server, server_response_pairs):
             mock.get(f"https://{server}/api?action=is-up", **response)
 
         assert find_server(servers) is expected_server
+
+
+def test_find_server__multiple_successes():
+    with requests_mock.Mocker() as mock:
+        mock.get(f"https://{SERVER_1}/api?action=is-up", exc=requests.exceptions.ConnectionError)
+        mock.get(f"https://{SERVER_2}/api?action=is-up", text="")
+        mock.get(f"https://{SERVER_3}/api?action=is-up", text="")
+        mock.get(f"https://{SERVER_4}/api?action=is-up", text="")
+
+        assert find_server(servers) == SERVER_2
diff --git a/monkey/tests/unit_tests/infection_monkey/network/test_info.py b/monkey/tests/unit_tests/infection_monkey/network/test_info.py
index 8dab89e4b..f0508ce98 100644
--- a/monkey/tests/unit_tests/infection_monkey/network/test_info.py
+++ b/monkey/tests/unit_tests/infection_monkey/network/test_info.py
@@ -3,7 +3,7 @@ from typing import Tuple
 
 import pytest
 
-from infection_monkey.network.info import get_free_tcp_port
+from infection_monkey.network.info import TCPPortSelector
 from infection_monkey.network.ports import COMMON_PORTS
 
 
@@ -13,28 +13,48 @@ class Connection:
 
 
 @pytest.mark.parametrize("port", COMMON_PORTS)
-def test_get_free_tcp_port__checks_common_ports(port: int, monkeypatch):
+def test_tcp_port_selector__checks_common_ports(port: int, monkeypatch):
+    tcp_port_selector = TCPPortSelector()
     unavailable_ports = [Connection(("", p)) for p in COMMON_PORTS if p is not port]
 
     monkeypatch.setattr(
         "infection_monkey.network.info.psutil.net_connections", lambda: unavailable_ports
     )
-    assert get_free_tcp_port() is port
+    assert tcp_port_selector.get_free_tcp_port() is port
 
 
-def test_get_free_tcp_port__checks_other_ports_if_common_ports_unavailable(monkeypatch):
+def test_tcp_port_selector__checks_other_ports_if_common_ports_unavailable(monkeypatch):
+    tcp_port_selector = TCPPortSelector()
     unavailable_ports = [Connection(("", p)) for p in COMMON_PORTS]
     monkeypatch.setattr(
         "infection_monkey.network.info.psutil.net_connections", lambda: unavailable_ports
     )
 
-    assert get_free_tcp_port() is not None
+    assert tcp_port_selector.get_free_tcp_port() is not None
 
 
-def test_get_free_tcp_port__none_if_no_available_ports(monkeypatch):
+def test_tcp_port_selector__none_if_no_available_ports(monkeypatch):
+    tcp_port_selector = TCPPortSelector()
     unavailable_ports = [Connection(("", p)) for p in range(65535)]
     monkeypatch.setattr(
         "infection_monkey.network.info.psutil.net_connections", lambda: unavailable_ports
     )
 
-    assert get_free_tcp_port() is None
+    assert tcp_port_selector.get_free_tcp_port() is None
+
+
+@pytest.mark.parametrize("common_port", COMMON_PORTS)
+def test_tcp_port_selector__checks_common_ports_leases(common_port: int, monkeypatch):
+    tcp_port_selector = TCPPortSelector()
+    unavailable_ports = [Connection(("", p)) for p in COMMON_PORTS if p is not common_port]
+    monkeypatch.setattr(
+        "infection_monkey.network.info.psutil.net_connections", lambda: unavailable_ports
+    )
+
+    free_port_1 = tcp_port_selector.get_free_tcp_port()
+    free_port_2 = tcp_port_selector.get_free_tcp_port()
+
+    assert free_port_1 == common_port
+    assert free_port_2 != common_port
+    assert free_port_2 is not None
+    assert free_port_2 not in COMMON_PORTS
diff --git a/monkey/tests/unit_tests/infection_monkey/utils/test_threading.py b/monkey/tests/unit_tests/infection_monkey/utils/test_threading.py
index 96a289096..05b813b66 100644
--- a/monkey/tests/unit_tests/infection_monkey/utils/test_threading.py
+++ b/monkey/tests/unit_tests/infection_monkey/utils/test_threading.py
@@ -1,8 +1,10 @@
 import logging
+from itertools import zip_longest
 from threading import Event, current_thread
 from typing import Any
 
 from infection_monkey.utils.threading import (
+    ThreadSafeIterator,
     create_daemon_thread,
     interruptible_function,
     interruptible_iter,
@@ -127,3 +129,11 @@ def test_interruptible_decorator_returns_default_value_on_interrupt():
 
     assert return_value == 777
     assert fn.call_count == 0
+
+
+def test_thread_safe_iterator():
+    test_list = [1, 2, 3, 4, 5]
+    tsi = ThreadSafeIterator(test_list.__iter__())
+
+    for actual, expected in zip_longest(tsi, test_list):
+        assert actual == expected