diff --git a/src/debugpy/server/api.py b/src/debugpy/server/api.py
index a1de5874..97cb13cc 100644
--- a/src/debugpy/server/api.py
+++ b/src/debugpy/server/api.py
@@ -156,7 +156,18 @@ def listen(address, settrace_kwargs, in_process_debug_adapter=False):
             block_until_connected=False,
             **settrace_kwargs
         )
-        return
+        # pydevd binds the listening socket on a background reader thread, so
+        # the OS-assigned port (when port=0 is passed) isn't visible from
+        # here directly. Wait for the socket to be ready and read the actual
+        # bound endpoint back from the global debugger.
+        pydb = get_global_debugger()
+        if pydb is not None:
+            pydb.wait_for_server_socket_ready()
+            actual_host, actual_port = pydb._server_socket_name
+        else:
+            actual_host, actual_port = host, port
+        listen.called = True
+        return actual_host, actual_port
 
     import subprocess
 
diff --git a/tests/debugpy/test_api.py b/tests/debugpy/test_api.py
new file mode 100644
index 00000000..48f1b41c
--- /dev/null
+++ b/tests/debugpy/test_api.py
@@ -0,0 +1,57 @@
+import pytest
+
+import debugpy.server.api as _api
+
+
+@pytest.fixture
+def no_settrace(monkeypatch):
+    # Avoid actually starting pydevd; we only care about listen()'s return value.
+    monkeypatch.setattr(_api, "_settrace", lambda **kwargs: None)
+    monkeypatch.setattr(_api.listen, "called", False)
+
+
+def test_listen_in_process_returns_endpoint(no_settrace):
+    # Regression test for #1656: listen(..., in_process_debug_adapter=True) used
+    # to return None, unlike the out-of-process path which returns (host, port).
+    endpoint = _api.listen(("127.0.0.1", 5678), in_process_debug_adapter=True)
+    assert endpoint == ("127.0.0.1", 5678)
+    assert _api.listen.called is True
+
+
+class _FakePyDB:
+    """Minimal stand-in for the global pydevd debugger.
+
+    Mirrors the bits of the real PyDB that listen()'s in-process path reads
+    after _settrace(): ``wait_for_server_socket_ready`` and
+    ``_server_socket_name`` (set by the reader thread once the listening
+    socket is bound).
+    """
+
+    def __init__(self, host, port):
+        self._server_socket_name = (host, port)
+
+    def wait_for_server_socket_ready(self):
+        return None
+
+
+@pytest.fixture
+def in_process_debugger(monkeypatch):
+    # Stub out _settrace (don't actually start pydevd) and inject a fake
+    # global debugger so that listen()'s in-process path can read the
+    # actual bound endpoint back from it.
+    monkeypatch.setattr(_api, "_settrace", lambda **kwargs: None)
+    monkeypatch.setattr(_api.listen, "called", False)
+    fake = _FakePyDB("127.0.0.1", 54321)
+    monkeypatch.setattr(_api, "get_global_debugger", lambda: fake)
+    return fake
+
+
+def test_listen_in_process_port_zero_resolves_bound_port(in_process_debugger):
+    # Regression test for #1656: when port=0 is passed, listen() must return
+    # the OS-assigned bound port rather than the literal 0.
+    endpoint = _api.listen(("127.0.0.1", 0), in_process_debug_adapter=True)
+    host, port = endpoint
+    assert host == "127.0.0.1"
+    assert isinstance(port, int)
+    assert port > 0
+    assert port == in_process_debugger._server_socket_name[1]