diff --git a/litellm/proxy/db/pgbouncer.py b/litellm/proxy/db/pgbouncer.py
index 313ab5967b3..be99c0eb60b 100644
--- a/litellm/proxy/db/pgbouncer.py
+++ b/litellm/proxy/db/pgbouncer.py
@@ -275,9 +275,9 @@ class PgBouncerProcess:
     Prisma reconnects by itself after a failed query, so a PgBouncer crash
     costs the requests in flight plus one failed query per idle pooled
     connection the crash severed, and nothing else once the replacement is
-    listening again. A replacement that cannot be spawned, exits again or
-    never starts listening is retried every ``restart_delay_seconds`` until
-    ``stop`` is called.
+    listening again. A replacement that cannot be spawned, finds its port
+    taken, exits again or never starts listening is retried every
+    ``restart_delay_seconds`` until ``stop`` is called.
     """
 
     def __init__(
@@ -300,12 +300,21 @@ class PgBouncerProcess:
         with self._lock:
             return None if self._process is None else self._process.pid
 
-    def _spawn(self) -> subprocess.Popen[bytes] | None:
-        """Start a child, or None once ``stop`` ran; both take the lock so no child can slip in after a stop."""
+    def _spawn(self) -> subprocess.Popen[bytes] | PgBouncerError | None:
+        """Start a child, or None once ``stop`` ran; both take the lock so no child can slip in after a stop.
+
+        The port has to be free first: a listener that is already there would
+        pass the readiness check while the child fails to bind.
+        """
         with self._lock:
             if self._stopping.is_set():
                 return None
-            process: Final = subprocess.Popen(self.argv)
+            if _port_open(self.port):
+                return PgBouncerError(f"{PGBOUNCER_LISTEN_ADDR}:{self.port} is already in use by another process")
+            try:
+                process: Final = subprocess.Popen(self.argv)
+            except OSError as spawn_error:
+                return PgBouncerError(f"could not start {self.argv[0]!r}: {spawn_error}")
             self._process = process
             return process
 
@@ -324,12 +333,11 @@ class PgBouncerProcess:
 
     def start(self) -> PgBouncerError | None:
         """Spawn PgBouncer, wait until it accepts connections, then supervise it from a daemon thread."""
-        try:
-            process: Final = self._spawn()
-        except OSError as spawn_error:
-            return PgBouncerError(f"could not start {self.argv[0]!r}: {spawn_error}")
+        process: Final = self._spawn()
         if process is None:
             return PgBouncerError("pgbouncer was stopped before it started")
+        if isinstance(process, PgBouncerError):
+            return process
         not_ready: Final = self._wait_ready(process)
         if not_ready is not None:
             self.stop()
@@ -356,13 +364,12 @@ class PgBouncerProcess:
 
     def _restart_after_delay(self) -> None:
         time.sleep(self.restart_delay_seconds)
-        try:
-            process: Final = self._spawn()
-        except OSError as spawn_error:
-            self._retry_restart(str(spawn_error))
-            return
+        process: Final = self._spawn()
         if process is None:
             return
+        if isinstance(process, PgBouncerError):
+            self._retry_restart(process.reason)
+            return
         not_ready: Final = self._wait_ready(process)
         if not_ready is None:
             self._watch(process)
diff --git a/tests/test_litellm/proxy/db/test_pgbouncer.py b/tests/test_litellm/proxy/db/test_pgbouncer.py
index 97d19c93634..21038ec6089 100644
--- a/tests/test_litellm/proxy/db/test_pgbouncer.py
+++ b/tests/test_litellm/proxy/db/test_pgbouncer.py
@@ -310,6 +310,39 @@ class TestPgBouncerProcess:
         assert isinstance(outcome, PgBouncerError)
         assert "/nonexistent/pgbouncer" in outcome.reason
 
+    def test_a_port_owned_by_someone_else_is_refused_before_spawning(self, tmp_path: Path):
+        with socket.socket() as squatter:
+            squatter.bind(("127.0.0.1", 0))
+            squatter.listen()
+            port: Final = squatter.getsockname()[1]
+            pooler: Final = PgBouncerProcess(argv=(str(_fake_pooler(tmp_path, port)),), port=port)
+            outcome: Final = pooler.start()
+        assert isinstance(outcome, PgBouncerError)
+        assert f"127.0.0.1:{port} is already in use" in outcome.reason
+        assert pooler.pid is None
+
+    def test_a_replacement_waits_until_a_squatter_leaves_the_port(
+        self, tmp_path: Path, caplog: pytest.LogCaptureFixture
+    ):
+        port: Final = _free_port()
+        pooler: Final = PgBouncerProcess(
+            argv=(str(_fake_pooler(tmp_path, port)),), port=port, restart_delay_seconds=0.5
+        )
+        assert pooler.start() is None
+        first_pid: Final = pooler.pid
+        assert first_pid is not None
+        os.kill(first_pid, signal.SIGKILL)
+        assert _wait_until(lambda: not _listening(port))
+        with socket.socket() as squatter, caplog.at_level(logging.ERROR, logger=verbose_proxy_logger.name):
+            squatter.setsockopt(socket.SOL_SOCKET, socket.SO_REUSEADDR, 1)
+            squatter.bind(("127.0.0.1", port))
+            squatter.listen()
+            assert _wait_until(lambda: any("already in use" in record.message for record in caplog.records))
+            assert pooler.pid == first_pid
+        assert _wait_until(lambda: pooler.pid not in (None, first_pid) and _listening(port))
+        pooler.stop()
+        assert _wait_until(lambda: not _listening(port))
+
     def test_a_pooler_that_never_listens_times_out(self, tmp_path: Path):
         port: Final = _free_port()
         pooler: Final = PgBouncerProcess(