diff --git a/muxplex/cli.py b/muxplex/cli.py
index 542b2e5..b02f344 100644
--- a/muxplex/cli.py
+++ b/muxplex/cli.py
@@ -162,6 +162,43 @@ def show_password() -> None:
         print("No password file found. Start muxplex to auto-generate one.")
 
 
+def _kill_stale_port_holder(port: int) -> None:
+    """Kill any existing process on *port* to prevent EADDRINUSE crash-loops.
+
+    On service restart (``systemctl restart muxplex``), the old process may still
+    be holding the port in TIME_WAIT state or simply not have exited yet.  Without
+    this guard the new process fails to bind, exits with status=1, and systemd
+    restarts it in an infinite loop (observed: 2075+ restarts before manual
+    intervention).
+
+    Uses ``lsof -ti :<port>`` to find occupants, sends SIGTERM, then waits 1 s
+    for the port to free.  Silently swallows all errors so that a missing ``lsof``
+    or a permission error never prevents the server from starting.
+    """
+    import signal
+    import time
+
+    try:
+        result = subprocess.run(
+            ["lsof", "-ti", f":{port}"],
+            capture_output=True,
+            text=True,
+            timeout=5,
+        )
+        if result.returncode == 0 and result.stdout.strip():
+            my_pid = os.getpid()
+            for pid_str in result.stdout.strip().split("\n"):
+                try:
+                    pid = int(pid_str.strip())
+                    if pid != my_pid:
+                        os.kill(pid, signal.SIGTERM)
+                except (ValueError, ProcessLookupError, PermissionError):
+                    pass
+            time.sleep(1)  # Brief wait for the port to be released
+    except Exception:
+        pass  # lsof not available or other error — proceed; uvicorn will fail naturally
+
+
 def serve(
     host: str | None = None,
     port: int | None = None,
@@ -188,6 +225,9 @@ def serve(
     os.environ["MUXPLEX_AUTH"] = auth
     os.environ["MUXPLEX_SESSION_TTL"] = str(session_ttl)
 
+    # Prevent crash-loop on restart: kill any stale process holding the port
+    _kill_stale_port_holder(port)
+
     from muxplex.main import app  # noqa: PLC0415
 
     print(f"  muxplex → http://{host}:{port}")
diff --git a/muxplex/service.py b/muxplex/service.py
index fadc0ff..2e98e64 100644
--- a/muxplex/service.py
+++ b/muxplex/service.py
@@ -27,6 +27,8 @@ Type=simple
 ExecStart={exec_start}
 Restart=on-failure
 RestartSec=5s
+TimeoutStopSec=10
+KillMode=mixed
 Environment=PATH={safe_path}
 
 [Install]
diff --git a/muxplex/tests/test_cli.py b/muxplex/tests/test_cli.py
index a7e6a5a..6b7b50d 100644
--- a/muxplex/tests/test_cli.py
+++ b/muxplex/tests/test_cli.py
@@ -1070,6 +1070,133 @@ def test_main_dispatches_to_generate_federation_key(monkeypatch):
     )
 
 
+# ---------------------------------------------------------------------------
+# task: port-in-use crash-loop prevention — _kill_stale_port_holder
+# ---------------------------------------------------------------------------
+
+
+def test_kill_stale_port_holder_exists():
+    """_kill_stale_port_holder must be importable from muxplex.cli."""
+    from muxplex.cli import _kill_stale_port_holder  # noqa: F401
+
+
+def test_kill_stale_port_holder_runs_lsof(monkeypatch):
+    """_kill_stale_port_holder must invoke lsof -ti :<port> to find occupying PIDs."""
+    import subprocess
+    import muxplex.cli as cli_mod
+
+    lsof_calls = []
+
+    def fake_run(cmd, **kw):
+        lsof_calls.append(cmd)
+        return type("R", (), {"returncode": 1, "stdout": "", "stderr": ""})()
+
+    monkeypatch.setattr(subprocess, "run", fake_run)
+
+    cli_mod._kill_stale_port_holder(8088)
+
+    assert any("lsof" in str(c) for c in lsof_calls), (
+        "_kill_stale_port_holder must call lsof to discover port occupants"
+    )
+    assert any("8088" in str(c) for c in lsof_calls), (
+        "_kill_stale_port_holder must include the port number in the lsof call"
+    )
+
+
+def test_kill_stale_port_holder_kills_foreign_pid(monkeypatch):
+    """_kill_stale_port_holder must send SIGTERM to PIDs that are not our own."""
+    import os
+    import signal
+    import subprocess
+    import muxplex.cli as cli_mod
+
+    foreign_pid = 99999
+    killed = []
+
+    def fake_run(cmd, **kw):
+        return type(
+            "R", (), {"returncode": 0, "stdout": f"{foreign_pid}\n", "stderr": ""}
+        )()
+
+    def fake_kill(pid, sig):
+        killed.append((pid, sig))
+
+    monkeypatch.setattr(subprocess, "run", fake_run)
+    monkeypatch.setattr(os, "kill", fake_kill)
+    monkeypatch.setattr(os, "getpid", lambda: 12345)  # not the same as foreign_pid
+
+    # Patch time.sleep so test doesn't actually sleep
+    import time
+
+    monkeypatch.setattr(time, "sleep", lambda _: None)
+
+    cli_mod._kill_stale_port_holder(8088)
+
+    assert (foreign_pid, signal.SIGTERM) in killed, (
+        f"Expected SIGTERM sent to foreign PID {foreign_pid}, got: {killed}"
+    )
+
+
+def test_kill_stale_port_holder_skips_own_pid(monkeypatch):
+    """_kill_stale_port_holder must NOT kill its own PID."""
+    import os
+    import subprocess
+    import muxplex.cli as cli_mod
+
+    my_pid = 12345
+    killed = []
+
+    def fake_run(cmd, **kw):
+        return type("R", (), {"returncode": 0, "stdout": f"{my_pid}\n", "stderr": ""})()
+
+    monkeypatch.setattr(subprocess, "run", fake_run)
+    monkeypatch.setattr(os, "kill", lambda pid, sig: killed.append(pid))
+    monkeypatch.setattr(os, "getpid", lambda: my_pid)
+
+    import time
+
+    monkeypatch.setattr(time, "sleep", lambda _: None)
+
+    cli_mod._kill_stale_port_holder(8088)
+
+    assert my_pid not in killed, "_kill_stale_port_holder must not kill its own PID"
+
+
+def test_kill_stale_port_holder_survives_lsof_not_available(monkeypatch):
+    """_kill_stale_port_holder must not raise when lsof is unavailable."""
+    import subprocess
+    import muxplex.cli as cli_mod
+
+    def fake_run(cmd, **kw):
+        raise FileNotFoundError("lsof not found")
+
+    monkeypatch.setattr(subprocess, "run", fake_run)
+
+    # Should not raise
+    cli_mod._kill_stale_port_holder(8088)
+
+
+def test_serve_calls_kill_stale_port_holder(tmp_path, monkeypatch):
+    """serve() must call _kill_stale_port_holder(port) before starting uvicorn."""
+    import muxplex.cli as cli_mod
+
+    settings_file = tmp_path / "settings.json"
+    monkeypatch.setattr("muxplex.settings.SETTINGS_PATH", settings_file)
+
+    killed_ports = []
+    monkeypatch.setattr(
+        cli_mod, "_kill_stale_port_holder", lambda port: killed_ports.append(port)
+    )
+
+    with patch("uvicorn.run"):
+        with patch.dict("sys.modules", {"muxplex.main": MagicMock()}):
+            cli_mod.serve(port=9876)
+
+    assert 9876 in killed_ports, (
+        "serve() must call _kill_stale_port_holder with the resolved port before uvicorn.run"
+    )
+
+
 def test_upgrade_uses_service_module_install(monkeypatch, capsys):
     """upgrade() must call muxplex.service.service_install."""
     import subprocess
diff --git a/muxplex/tests/test_service.py b/muxplex/tests/test_service.py
index b835416..dcce621 100644
--- a/muxplex/tests/test_service.py
+++ b/muxplex/tests/test_service.py
@@ -541,6 +541,41 @@ def test_systemd_logs_handles_keyboard_interrupt(monkeypatch):
     svc._systemd_logs()
 
 
+# ---------------------------------------------------------------------------
+# task: port-in-use crash-loop prevention — TimeoutStopSec in systemd unit
+# ---------------------------------------------------------------------------
+
+
+def test_systemd_unit_template_has_timeout_stop_sec():
+    """_SYSTEMD_UNIT_TEMPLATE must include TimeoutStopSec to SIGKILL stale process."""
+    import muxplex.service as svc
+
+    assert "TimeoutStopSec" in svc._SYSTEMD_UNIT_TEMPLATE, (
+        "_SYSTEMD_UNIT_TEMPLATE must include TimeoutStopSec so systemd sends SIGKILL "
+        "if the old process does not exit on SIGTERM within the configured time"
+    )
+
+
+def test_systemd_install_writes_timeout_stop_sec(monkeypatch, tmp_path):
+    """The written unit file must contain TimeoutStopSec."""
+    import muxplex.service as svc
+
+    unit_dir = tmp_path / "systemd" / "user"
+    unit_path = unit_dir / "muxplex.service"
+
+    monkeypatch.setattr(svc, "_SYSTEMD_UNIT_DIR", unit_dir)
+    monkeypatch.setattr(svc, "_SYSTEMD_UNIT_PATH", unit_path)
+
+    calls = []
+    monkeypatch.setattr(subprocess, "run", lambda cmd, **kw: calls.append(list(cmd)))
+    monkeypatch.setattr(svc, "_prompt_host_if_localhost", lambda: None)
+
+    svc._systemd_install()
+
+    content = unit_path.read_text()
+    assert "TimeoutStopSec" in content, "Written unit file must contain TimeoutStopSec"
+
+
 def test_launchd_logs_handles_keyboard_interrupt(monkeypatch):
     """service logs must exit cleanly on Ctrl+C on macOS."""
     import muxplex.service as svc