diff --git a/devlib/connection.py b/devlib/connection.py
index 020db209d..8c4105591 100644
--- a/devlib/connection.py
+++ b/devlib/connection.py
@@ -62,10 +62,11 @@ class ConnectionBase(InitCheckpoint):
     Base class for all connections.
     """
     def __init__(self):
-        self._current_bg_cmds = WeakSet()
+        self._current_bg_cmds = set()
         self._closed = False
         self._close_lock = threading.Lock()
         self.busybox = None
+        self.logger = logging.getLogger('Connection')
 
     def cancel_running_command(self):
         bg_cmds = set(self._current_bg_cmds)
@@ -83,11 +84,21 @@ def _close(self):
         """
 
     def close(self):
+
+        def finish_bg():
+            bg_cmds = set(self._current_bg_cmds)
+            n = len(bg_cmds)
+            if n:
+                self.logger.debug(f'Canceling {n} background commands before closing connection')
+            for bg_cmd in bg_cmds:
+                bg_cmd.cancel()
+
         # Locking the closing allows any thread to safely call close() as long
         # as the connection can be closed from a thread that is not the one it
         # started its life in.
         with self._close_lock:
             if not self._closed:
+                finish_bg()
                 self._close()
                 self._closed = True
 
@@ -109,7 +120,34 @@ class BackgroundCommand(ABC):
     Instances of this class can be used as context managers, with the same
     semantic as :class:`subprocess.Popen`.
     """
+
+    def __init__(self, conn):
+        self.conn = conn
+
+        # Poll currently opened background commands on that connection to make
+        # them deregister themselves if they are completed. This avoids
+        # accumulating terminated commands and therefore leaking associated
+        # resources if the user is not careful and does not use the context
+        # manager API.
+        for bg_cmd in set(conn._current_bg_cmds):
+            try:
+                bg_cmd.poll()
+            # We don't want anything to fail here because of another command
+            except Exception:
+                pass
+
+        conn._current_bg_cmds.add(self)
+
+    def _deregister(self):
+        try:
+            self.conn._current_bg_cmds.remove(self)
+        except KeyError:
+            pass
+
     @abstractmethod
+    def _send_signal(self, sig):
+        pass
+
     def send_signal(self, sig):
         """
         Send a POSIX signal to the background command's process group ID
@@ -118,6 +156,11 @@ def send_signal(self, sig):
         :param signal: Signal to send.
         :type signal: signal.Signals
         """
+        try:
+            self._send_signal(signal.SIGKILL)
+        finally:
+            # Deregister if the command has finished
+            self.poll()
 
     def kill(self):
         """
@@ -130,8 +173,11 @@ def cancel(self, kill_timeout=_KILL_TIMEOUT):
         Try to gracefully terminate the process by sending ``SIGTERM``, then
         waiting for ``kill_timeout`` to send ``SIGKILL``.
         """
-        if self.poll() is None:
-            self._cancel(kill_timeout=kill_timeout)
+        try:
+            if self.poll() is None:
+                self._cancel(kill_timeout=kill_timeout)
+        finally:
+            self._deregister()
 
     @abstractmethod
     def _cancel(self, kill_timeout):
@@ -141,10 +187,17 @@ def _cancel(self, kill_timeout):
         pass
 
     @abstractmethod
+    def _wait(self):
+        pass
+
     def wait(self):
         """
         Block until the background command completes, and return its exit code.
         """
+        try:
+            self._wait()
+        finally:
+            self._deregister()
 
     def communicate(self, input=b'', timeout=None):
         """
@@ -162,10 +215,17 @@ def _communicate(self, input, timeout):
         pass
 
     @abstractmethod
+    def _poll(self):
+        pass
+
     def poll(self):
         """
         Return exit code if the command has exited, None otherwise.
         """
+        retcode = self._poll()
+        if retcode is not None:
+            self._deregister()
+        return retcode
 
     @property
     @abstractmethod
@@ -202,6 +262,9 @@ def pid(self):
         """
 
     @abstractmethod
+    def _close(self):
+        pass
+
     def close(self):
         """
         Close all opened streams and then wait for command completion.
@@ -211,6 +274,10 @@ def close(self):
         .. note:: If the command is writing to its stdout/stderr, it might be
             blocked on that and die when the streams are closed.
         """
+        try:
+            return self._close()
+        finally:
+            self._deregister()
 
     def __enter__(self):
         return self
@@ -224,10 +291,11 @@ class PopenBackgroundCommand(BackgroundCommand):
     :class:`subprocess.Popen`-based background command.
     """
 
-    def __init__(self, popen):
+    def __init__(self, conn, popen):
+        super().__init__(conn=conn)
         self.popen = popen
 
-    def send_signal(self, sig):
+    def _send_signal(self, sig):
         return os.killpg(self.popen.pid, sig)
 
     @property
@@ -246,13 +314,13 @@ def stderr(self):
     def pid(self):
         return self.popen.pid
 
-    def wait(self):
+    def _wait(self):
         return self.popen.wait()
 
     def _communicate(self, input, timeout):
         return _popen_communicate(self, self.popen, input, timeout)
 
-    def poll(self):
+    def _poll(self):
         return self.popen.poll()
 
     def _cancel(self, kill_timeout):
@@ -263,26 +331,24 @@ def _cancel(self, kill_timeout):
         except subprocess.TimeoutExpired:
             os.killpg(os.getpgid(popen.pid), signal.SIGKILL)
 
-    def close(self):
+    def _close(self):
         self.popen.__exit__(None, None, None)
         return self.popen.returncode
 
     def __enter__(self):
+        super().__enter__()
         self.popen.__enter__()
         return self
 
-    def __exit__(self, *args, **kwargs):
-        self.popen.__exit__(*args, **kwargs)
-
 
 class ParamikoBackgroundCommand(BackgroundCommand):
     """
     :mod:`paramiko`-based background command.
     """
     def __init__(self, conn, chan, pid, as_root, cmd, stdin, stdout, stderr, redirect_thread):
+        super().__init__(conn=conn)
         self.chan = chan
         self.as_root = as_root
-        self.conn = conn
         self._pid = pid
         self._stdin = stdin
         self._stdout = stdout
@@ -290,7 +356,7 @@ def __init__(self, conn, chan, pid, as_root, cmd, stdin, stdout, stderr, redirec
         self.redirect_thread = redirect_thread
         self.cmd = cmd
 
-    def send_signal(self, sig):
+    def _send_signal(self, sig):
         # If the command has already completed, we don't want to send a signal
         # to another process that might have gotten that PID in the meantime.
         if self.poll() is not None:
@@ -304,7 +370,7 @@ def send_signal(self, sig):
     def pid(self):
         return self._pid
 
-    def wait(self):
+    def _wait(self):
         status = self.chan.recv_exit_status()
         # Ensure that the redirection thread is finished copying the content
         # from paramiko to the pipe.
@@ -390,7 +456,7 @@ def create_out():
         else:
             return (_stdout, _stderr)
 
-    def poll(self):
+    def _poll(self):
         # Wait for the redirection thread to finish, otherwise we would
         # indicate the caller that the command is finished and that the streams
         # are safe to drain, but actually the redirection thread is not
@@ -424,7 +490,7 @@ def stdout(self):
     def stderr(self):
         return self._stderr
 
-    def close(self):
+    def _close(self):
         for x in (self.stdin, self.stdout, self.stderr):
             if x is not None:
                 x.close()
@@ -443,12 +509,12 @@ class AdbBackgroundCommand(BackgroundCommand):
     """
 
     def __init__(self, conn, adb_popen, pid, as_root):
-        self.conn = conn
+        super().__init__(conn=conn)
         self.as_root = as_root
         self.adb_popen = adb_popen
         self._pid = pid
 
-    def send_signal(self, sig):
+    def _send_signal(self, sig):
         self.conn.execute(
             _kill_pgid_cmd(self.pid, sig, self.conn.busybox),
             as_root=self.as_root,
@@ -470,14 +536,13 @@ def stderr(self):
     def pid(self):
         return self._pid
 
-    def wait(self):
+    def _wait(self):
         return self.adb_popen.wait()
 
     def _communicate(self, input, timeout):
         return _popen_communicate(self, self.adb_popen, input, timeout)
 
-
-    def poll(self):
+    def _poll(self):
         return self.adb_popen.poll()
 
     def _cancel(self, kill_timeout):
@@ -488,17 +553,15 @@ def _cancel(self, kill_timeout):
             self.send_signal(signal.SIGKILL)
             self.adb_popen.kill()
 
-    def close(self):
+    def _close(self):
         self.adb_popen.__exit__(None, None, None)
         return self.adb_popen.returncode
 
     def __enter__(self):
+        super().__enter__()
         self.adb_popen.__enter__()
         return self
 
-    def __exit__(self, *args, **kwargs):
-        self.adb_popen.__exit__(*args, **kwargs)
-
 
 class TransferManagerBase(ABC):
 
diff --git a/devlib/host.py b/devlib/host.py
index a6796da5f..68c535d39 100644
--- a/devlib/host.py
+++ b/devlib/host.py
@@ -141,8 +141,7 @@ def preexec_fn():
             shell=True,
             preexec_fn=preexec_fn,
         )
-        bg_cmd = PopenBackgroundCommand(popen)
-        self._current_bg_cmds.add(bg_cmd)
+        bg_cmd = PopenBackgroundCommand(self, popen)
         return bg_cmd
 
     def _close(self):
diff --git a/devlib/utils/android.py b/devlib/utils/android.py
index b57910da6..1cae582e9 100755
--- a/devlib/utils/android.py
+++ b/devlib/utils/android.py
@@ -334,7 +334,12 @@ def _push_pull(self, action, sources, dest, timeout):
             adb_command(self.device, command, timeout=timeout, adb_server=self.adb_server)
         else:
             with self.transfer_mgr.manage(sources, dest, action):
-                bg_cmd = adb_command_background(self.device, command, adb_server=self.adb_server)
+                bg_cmd = adb_command_background(
+                    device=self.device,
+                    conn=self,
+                    command=command,
+                    adb_server=self.adb_server
+                )
                 self.transfer_mgr.set_transfer_and_wait(bg_cmd)
 
     # pylint: disable=unused-argument
@@ -363,7 +368,6 @@ def background(self, command, stdout=subprocess.PIPE, stderr=subprocess.PIPE, as
         if as_root and self.connected_as_root:
             as_root = False
         bg_cmd = self._background(command, stdout, stderr, as_root)
-        self._current_bg_cmds.add(bg_cmd)
         return bg_cmd
 
     def _background(self, command, stdout, stderr, as_root):
@@ -692,11 +696,11 @@ def adb_command(device, command, timeout=None, adb_server=None):
     return output
 
 
-def adb_command_background(device, command, adb_server=None):
+def adb_command_background(device, conn, command, adb_server=None):
     full_command = get_adb_command(device, command, adb_server)
     logger.debug(full_command)
-    proc = get_subprocess(full_command, shell=True)
-    cmd = PopenBackgroundCommand(proc)
+    popen = get_subprocess(full_command, shell=True)
+    cmd = PopenBackgroundCommand(conn=conn, popen=popen)
     return cmd
 
 
diff --git a/devlib/utils/ssh.py b/devlib/utils/ssh.py
index 39d704645..b8485219c 100644
--- a/devlib/utils/ssh.py
+++ b/devlib/utils/ssh.py
@@ -553,10 +553,7 @@ def execute(self, command, timeout=None, check_exit_code=True,
 
     def background(self, command, stdout=subprocess.PIPE, stderr=subprocess.PIPE, as_root=False):
         with _handle_paramiko_exceptions(command):
-            bg_cmd = self._background(command, stdout, stderr, as_root)
-
-        self._current_bg_cmds.add(bg_cmd)
-        return bg_cmd
+            return self._background(command, stdout, stderr, as_root)
 
     def _background(self, command, stdout, stderr, as_root):
         orig_command = command
@@ -696,9 +693,6 @@ def callback(out_streams, name, chunk):
     def _close(self):
         logger.debug('Logging out {}@{}'.format(self.username, self.host))
         with _handle_paramiko_exceptions():
-            bg_cmds = set(self._current_bg_cmds)
-            for bg_cmd in bg_cmds:
-                bg_cmd.close()
             self.client.close()
 
     def _execute_command(self, command, as_root, log, timeout, executor):