diff --git a/hermes_cli/gateway.py b/hermes_cli/gateway.py
index caa0b6133..28ef9cfb6 100644
--- a/hermes_cli/gateway.py
+++ b/hermes_cli/gateway.py
@@ -4082,6 +4082,11 @@ def launchd_restart():
         print("↻ launchd job was unloaded; reloading")
         plist_path = get_launchd_plist_path()
         try:
+            subprocess.run(
+                ["launchctl", "bootout", target],
+                check=False,
+                timeout=90,
+            )
             subprocess.run(
                 ["launchctl", "bootstrap", _launchd_domain(), str(plist_path)],
                 check=True,
diff --git a/tests/hermes_cli/test_gateway_service.py b/tests/hermes_cli/test_gateway_service.py
index fa7d2e982..55753f3e1 100644
--- a/tests/hermes_cli/test_gateway_service.py
+++ b/tests/hermes_cli/test_gateway_service.py
@@ -1077,6 +1077,46 @@ class TestLaunchdServiceRecovery:
         assert spawned == [True]
         assert gateway_cli._launchd_unsupported_marker_exists()
 
+    def test_launchd_restart_boots_out_stale_registration_before_bootstrap(
+        self, tmp_path, monkeypatch
+    ):
+        plist_path = tmp_path / "ai.hermes.gateway.plist"
+        plist_path.write_text(gateway_cli.generate_launchd_plist(), encoding="utf-8")
+        label = gateway_cli.get_launchd_label()
+        domain = gateway_cli._launchd_domain()
+        target = f"{domain}/{label}"
+
+        monkeypatch.setattr(gateway_cli, "get_launchd_plist_path", lambda: plist_path)
+        monkeypatch.setattr(gateway_cli, "_get_restart_drain_timeout", lambda: 5.0)
+        monkeypatch.setattr(gateway_cli, "_request_gateway_self_restart", lambda pid: False)
+        monkeypatch.setattr(
+            gateway_cli, "_wait_for_gateway_exit", lambda timeout, force_after=None: True
+        )
+        monkeypatch.setattr(gateway_cli, "terminate_pid", lambda pid, force=False: None)
+        monkeypatch.setattr("gateway.status.get_running_pid", lambda: 321)
+
+        calls = []
+
+        def fake_run(cmd, check=False, **kwargs):
+            if cmd and cmd[0] == "launchctl":
+                calls.append(cmd)
+            if cmd == ["launchctl", "kickstart", "-k", target]:
+                raise gateway_cli.subprocess.CalledProcessError(
+                    3, cmd, stderr="Could not find service"
+                )
+            return SimpleNamespace(returncode=0, stdout="", stderr="")
+
+        monkeypatch.setattr(gateway_cli.subprocess, "run", fake_run)
+
+        gateway_cli.launchd_restart()
+
+        assert calls == [
+            ["launchctl", "kickstart", "-k", target],
+            ["launchctl", "bootout", target],
+            ["launchctl", "bootstrap", domain, str(plist_path)],
+            ["launchctl", "kickstart", target],
+        ]
+
     def test_launchd_stop_tolerates_domain_unsupported_bootout(self, monkeypatch, capsys):
         """bootout exit 125 (macOS 26) must fall through to PID-based kill, not raise."""
         def fake_run(cmd, check=False, **kwargs):