diff --git a/src/debugpy/adapter/clients.py b/src/debugpy/adapter/clients.py
index ada460edf..43b47d091 100644
--- a/src/debugpy/adapter/clients.py
+++ b/src/debugpy/adapter/clients.py
@@ -11,7 +11,7 @@
 import debugpy
 from debugpy import adapter, common, launcher
 from debugpy.common import json, log, messaging, sockets
-from debugpy.adapter import components, servers, sessions
+from debugpy.adapter import clients, components, launchers, servers, sessions
 
 
 class Client(components.Component):
@@ -110,6 +110,7 @@ def __init__(self, sock):
                 "data": {"packageVersion": debugpy.__version__},
             },
         )
+        self.report_sockets()
 
     def propagate_after_start(self, event):
         # pydevd starts sending events as soon as we connect, but the client doesn't
@@ -701,6 +702,25 @@ def disconnect_request(self, request):
     def disconnect(self):
         super().disconnect()
 
+    def report_sockets(self):
+        sockets = [
+            {
+                "host": host,
+                "port": port,
+                "internal": listener is not clients.listener,
+            }
+            for listener in [clients.listener, launchers.listener, servers.listener]
+            if listener is not None
+            for (host, port) in [listener.getsockname()]
+        ]
+
+        self.channel.send_event(
+            "debugpySockets",
+            {
+                "sockets": sockets
+            },
+        )
+
     def notify_of_subprocess(self, conn):
         log.info("{1} is a subprocess of {0}.", self, conn)
         with self.session:
@@ -752,11 +772,16 @@ def notify_of_subprocess(self, conn):
 def serve(host, port):
     global listener
     listener = sockets.serve("Client", Client, host, port)
+    sessions.report_sockets()
     return listener.getsockname()
 
 
 def stop_serving():
-    try:
-        listener.close()
-    except Exception:
-        log.swallow_exception(level="warning")
+    global listener
+    if listener is not None:
+        try:
+            listener.close()
+        except Exception:
+            log.swallow_exception(level="warning")
+        listener = None
+    sessions.report_sockets()
diff --git a/src/debugpy/adapter/launchers.py b/src/debugpy/adapter/launchers.py
index 444e54dd9..38a990d76 100644
--- a/src/debugpy/adapter/launchers.py
+++ b/src/debugpy/adapter/launchers.py
@@ -8,7 +8,9 @@
 
 from debugpy import adapter, common
 from debugpy.common import log, messaging, sockets
-from debugpy.adapter import components, servers
+from debugpy.adapter import components, servers, sessions
+
+listener = None
 
 
 class Launcher(components.Component):
@@ -76,6 +78,8 @@ def spawn_debuggee(
     console_title,
     sudo,
 ):
+    global listener
+
     # -E tells sudo to propagate environment variables to the target process - this
     # is necessary for launcher to get DEBUGPY_LAUNCHER_PORT and DEBUGPY_LOG_DIR.
     cmdline = ["sudo", "-E"] if sudo else []
@@ -101,6 +105,7 @@ def on_launcher_connected(sock):
         raise start_request.cant_handle(
             "{0} couldn't create listener socket for launcher: {1}", session, exc
         )
+    sessions.report_sockets()
 
     try:
         launcher_host, launcher_port = listener.getsockname()
@@ -189,3 +194,5 @@ def on_launcher_connected(sock):
 
     finally:
         listener.close()
+        listener = None
+        sessions.report_sockets()
diff --git a/src/debugpy/adapter/servers.py b/src/debugpy/adapter/servers.py
index 47f684a04..025823616 100644
--- a/src/debugpy/adapter/servers.py
+++ b/src/debugpy/adapter/servers.py
@@ -13,7 +13,7 @@
 import debugpy
 from debugpy import adapter
 from debugpy.common import json, log, messaging, sockets
-from debugpy.adapter import components
+from debugpy.adapter import components, sessions
 import traceback
 import io
 
@@ -394,6 +394,7 @@ def disconnect(self):
 def serve(host="127.0.0.1", port=0):
     global listener
     listener = sockets.serve("Server", Connection, host, port)
+    sessions.report_sockets()
     return listener.getsockname()
 
 
@@ -409,6 +410,7 @@ def stop_serving():
             listener = None
     except Exception:
         log.swallow_exception(level="warning")
+    sessions.report_sockets()
 
 
 def connections():
diff --git a/src/debugpy/adapter/sessions.py b/src/debugpy/adapter/sessions.py
index 0abebcc8c..873617b2c 100644
--- a/src/debugpy/adapter/sessions.py
+++ b/src/debugpy/adapter/sessions.py
@@ -282,3 +282,10 @@ def wait_until_ended():
                 return
             _sessions_changed.clear()
         _sessions_changed.wait()
+
+
+def report_sockets():
+    for session in _sessions:
+        client = session.client
+        if client is not None:
+            client.report_sockets()
diff --git a/tests/debug/session.py b/tests/debug/session.py
index 21caeebaa..e9e0670e5 100644
--- a/tests/debug/session.py
+++ b/tests/debug/session.py
@@ -102,6 +102,11 @@ def __init__(self, debug_config=None):
         self.adapter = None
         """psutil.Popen instance for the adapter process."""
 
+        self.expected_adapter_sockets = {
+            "client": {"host": some.str, "port": some.int, "internal": False},
+        }
+        """The sockets which the adapter is expected to report."""
+
         self.adapter_endpoints = None
         """Name of the file that contains the adapter endpoints information.
 
@@ -183,6 +188,7 @@ def __init__(self, debug_config=None):
                 timeline.Event("module"),
                 timeline.Event("continued"),
                 timeline.Event("debugpyWaitingForServer"),
+                timeline.Event("debugpySockets"),
                 timeline.Event("thread", some.dict.containing({"reason": "started"})),
                 timeline.Event("thread", some.dict.containing({"reason": "exited"})),
                 timeline.Event("output", some.dict.containing({"category": "stdout"})),
@@ -352,7 +358,9 @@ def _make_env(self, base_env, codecov=True):
         return env
 
     def _make_python_cmdline(self, exe, *args):
-        return [str(s.strpath if isinstance(s, py.path.local) else s) for s in [exe, *args]]
+        return [
+            str(s.strpath if isinstance(s, py.path.local) else s) for s in [exe, *args]
+        ]
 
     def spawn_debuggee(self, args, cwd=None, exe=sys.executable, setup=None):
         assert self.debuggee is None
@@ -406,7 +414,9 @@ def spawn_adapter(self, args=()):
         assert self.adapter is None
         assert self.channel is None
 
-        args = self._make_python_cmdline(sys.executable, os.path.dirname(debugpy.adapter.__file__), *args)
+        args = self._make_python_cmdline(
+            sys.executable, os.path.dirname(debugpy.adapter.__file__), *args
+        )
         env = self._make_env(self.spawn_adapter.env)
 
         log.info(
@@ -436,6 +446,16 @@ def connect_to_adapter(self, address):
         self.before_connect(address)
         host, port = address
         log.info("Connecting to {0} at {1}:{2}", self.adapter_id, host, port)
+
+        self.expected_adapter_sockets["client"]["port"] = port
+
+        # If we're attaching, the server is already started, so it should be reported.
+        self.expected_adapter_sockets["server"] = {
+            "host": some.str,
+            "port": some.str,
+            "internal": True,
+        }
+
         sock = sockets.create_client()
         sock.connect(address)
 
@@ -483,16 +503,54 @@ def send_request(self, command, arguments=None, proceed=True):
 
     def _process_event(self, event):
         occ = self.timeline.record_event(event, block=False)
+
         if event.event == "exited":
             self.observe(occ)
             self.exit_code = event("exitCode", int)
             self.exit_reason = event("reason", str, optional=True)
             assert self.exit_code == self.expected_exit_code
+
+        elif event.event == "terminated":
+            # Server socket should be closed next.
+            self.expected_adapter_sockets.pop("server", None)
+
         elif event.event == "debugpyAttach":
             self.observe(occ)
             pid = event("subProcessId", int)
             watchdog.register_spawn(pid, f"{self.debuggee_id}-subprocess-{pid}")
 
+        elif event.event == "debugpySockets":
+            sockets = list(event("sockets", json.array(json.object())))
+            for purpose, expected_socket in self.expected_adapter_sockets.items():
+                if expected_socket is None:
+                    continue
+                socket = None
+                for socket in sockets:
+                    if socket == expected_socket:
+                        break
+                assert (
+                    socket is not None
+                ), f"Expected {purpose} socket {expected_socket} not reported by adapter"
+                sockets.remove(socket)
+            assert not sockets, f"Unexpected sockets reported by adapter: {sockets}"
+
+            if (
+                self.start_request is not None
+                and self.start_request.command == "launch"
+            ):
+                if "launcher" in self.expected_adapter_sockets:
+                    # If adapter has just reported the launcher socket, it shouldn't be
+                    # reported thereafter.
+                    self.expected_adapter_sockets["launcher"] = None
+                elif "server" in self.expected_adapter_sockets:
+                    # If adapter just reported the server socket, the next event should
+                    # report the launcher socket.
+                    self.expected_adapter_sockets["launcher"] = {
+                        "host": some.str,
+                        "port": some.int,
+                        "internal": False,
+                    }
+
     def run_in_terminal(self, args, cwd, env):
         exe = args.pop(0)
         self.spawn_debuggee.env.update(env)
@@ -514,10 +572,12 @@ def _process_request(self, request):
             except Exception as exc:
                 log.swallow_exception('"runInTerminal" failed:')
                 raise request.cant_handle(str(exc))
+
         elif request.command == "startDebugging":
             pid = request("configuration", dict)("subProcessId", int)
             watchdog.register_spawn(pid, f"{self.debuggee_id}-subprocess-{pid}")
             return {}
+
         else:
             raise request.isnt_valid("not supported")
 
@@ -549,7 +609,8 @@ def _start_channel(self, stream):
         self.channel.start()
 
         self.wait_for_next(
-            timeline.Event(
+            timeline.Event("debugpySockets")
+            & timeline.Event(
                 "output",
                 {
                     "category": "telemetry",
@@ -632,6 +693,15 @@ def request_launch(self):
             # If specified, launcher will use it in lieu of PYTHONPATH it inherited
             # from the adapter when spawning debuggee, so we need to adjust again.
             self.config.env.prepend_to("PYTHONPATH", DEBUGGEE_PYTHONPATH.strpath)
+
+        # Adapter is going to start listening for server and spawn the launcher at
+        # this point. Server socket gets reported first.
+        self.expected_adapter_sockets["server"] = {
+            "host": some.str,
+            "port": some.int,
+            "internal": True,
+        }
+
         return self._request_start("launch")
 
     def request_attach(self):
@@ -787,7 +857,9 @@ def wait_for_stop(
         return StopInfo(stopped, frames, tid, fid)
 
     def wait_for_next_subprocess(self):
-        message = self.timeline.wait_for_next(timeline.Event("debugpyAttach") | timeline.Request("startDebugging"))
+        message = self.timeline.wait_for_next(
+            timeline.Event("debugpyAttach") | timeline.Request("startDebugging")
+        )
         if isinstance(message, timeline.EventOccurrence):
             config = message.body
             assert "request" in config