diff --git a/hermes_cli/gateway.py b/hermes_cli/gateway.py
index 7a9951dd5..bd970d9ca 100644
--- a/hermes_cli/gateway.py
+++ b/hermes_cli/gateway.py
@@ -3588,6 +3588,86 @@ def _launchctl_bootstrap(
         )
 
 
+def _launchd_reload_log_path() -> Path:
+    """Path the launchd reload watchdog tails for persistent-orphan detection."""
+    return get_hermes_home() / "logs" / "launchd-reload.log"
+
+
+def _append_launchd_reload_log(message: str) -> None:
+    """Append a timestamped line to the launchd reload log (best-effort)."""
+    path = _launchd_reload_log_path()
+    try:
+        path.parent.mkdir(parents=True, exist_ok=True)
+        from datetime import datetime as _dt
+
+        stamp = _dt.now().astimezone().strftime("%Y-%m-%d %H:%M:%S %z")
+        with path.open("a", encoding="utf-8") as fh:
+            fh.write(f"[{stamp}] {message}\n")
+    except OSError:
+        pass
+
+
+def _launchctl_label_registered(label: str) -> bool:
+    """True when ``launchctl list <label>`` reports the job as registered."""
+    try:
+        result = subprocess.run(
+            ["launchctl", "list", label],
+            check=False,
+            timeout=10,
+            stdout=subprocess.DEVNULL,
+            stderr=subprocess.DEVNULL,
+        )
+        return result.returncode == 0
+    except (subprocess.TimeoutExpired, OSError):
+        return False
+
+
+def _retry_launchctl_bootstrap_until_registered(
+    domain: str, plist_path, label: str, *, deadline: float
+) -> bool:
+    """Bootstrap with retry until the label is registered or ``deadline`` passes.
+
+    Wraps :func:`_launchctl_bootstrap` (which already recovers the EIO
+    "already loaded" case) in a wall-clock retry loop for the *transient*
+    failure mode: under high load or a launchd race the bootstrap can fail
+    even after ``bootout`` already tore down the prior registration, leaving
+    the service orphaned from ``KeepAlive`` supervision. The reported incident
+    happened during a graceful drain (default ``agent.restart_drain_timeout``
+    = 180s), so a fixed ~10s window is too short — retry until ``deadline``.
+
+    Both ``CalledProcessError`` and ``TimeoutExpired`` are treated as
+    retryable: a ``bootstrap`` that times out after ``bootout`` still leaves
+    the service unloaded, so it must be retried, not allowed to escape. On
+    each failure a timestamped line is appended to the reload log; success is
+    confirmed with ``launchctl list`` (not merely a zero bootstrap exit).
+    Returns True once the label is registered, False if the deadline is hit.
+    """
+    attempt = 0
+    while True:
+        attempt += 1
+        try:
+            _launchctl_bootstrap(domain, plist_path, label, timeout=30)
+            if _launchctl_label_registered(label):
+                return True
+            _append_launchd_reload_log(
+                f"bootstrap attempt {attempt} exited 0 but {domain}/{label} "
+                f"is not registered (launchctl list) — retrying"
+            )
+        except subprocess.CalledProcessError as exc:
+            _append_launchd_reload_log(
+                f"bootstrap attempt {attempt} failed (rc={exc.returncode}) "
+                f"for {domain}/{label} — retrying"
+            )
+        except subprocess.TimeoutExpired:
+            _append_launchd_reload_log(
+                f"bootstrap attempt {attempt} timed out for {domain}/{label} "
+                f"— retrying"
+            )
+        if time.monotonic() >= deadline:
+            return False
+        time.sleep(2)
+
+
 # ── launchd unsupported marker ─────────────────────────────────────────────
 # When launchd can't manage the domain on this host (error 5/125, macOS 26+),
 # we write a persistent marker so `launchd_status()` can explain that launchd
@@ -3871,18 +3951,25 @@ def refresh_launchd_plist_if_needed() -> bool:
             reload_log_path.parent.mkdir(parents=True, exist_ok=True)
         except OSError:
             pass
+        # Retry until launchctl LISTS the label (not merely a zero bootstrap
+        # exit) or the drain window elapses. The failure happens while the old
+        # gateway is still draining (default agent.restart_drain_timeout=180s),
+        # so a fixed ~10s window is too short — bound by that budget instead.
+        _reload_budget = int(max(30.0, _get_restart_drain_timeout()))
         reload_script = (
             f"sleep 2; "
             f"launchctl bootout {shlex.quote(target)} 2>/dev/null; "
             f"sleep 1; "
-            f"for _i in 1 2 3 4 5; do "
-            f"  launchctl bootstrap {shlex.quote(domain)} {shlex.quote(str(plist_path))} 2>/dev/null && break; "
-            f"  rc=$?; "
-            f"  echo \"[$(date '+%Y-%m-%d %H:%M:%S %z')] bootstrap attempt $_i failed (rc=$rc) for {shlex.quote(target)}\" >> {shlex.quote(str(reload_log_path))}; "
+            f"_deadline=$(($(date +%s) + {_reload_budget})); "
+            f"while :; do "
+            f"  launchctl bootstrap {shlex.quote(domain)} {shlex.quote(str(plist_path))} 2>/dev/null; "
+            f"  if launchctl list {shlex.quote(label)} >/dev/null 2>&1; then break; fi; "
+            f"  echo \"[$(date '+%Y-%m-%d %H:%M:%S %z')] bootstrap not yet registered for {shlex.quote(target)} — retrying\" >> {shlex.quote(str(reload_log_path))}; "
+            f"  if [ $(date +%s) -ge $_deadline ]; then break; fi; "
             f"  sleep 2; "
             f"done; "
             f"if ! launchctl list {shlex.quote(label)} >/dev/null 2>&1; then "
-            f"  echo \"[$(date '+%Y-%m-%d %H:%M:%S %z')] FAILED launchd reload for {shlex.quote(target)} — service NOT registered after retries\" >> {shlex.quote(str(reload_log_path))}; "
+            f"  echo \"[$(date '+%Y-%m-%d %H:%M:%S %z')] FAILED launchd reload for {shlex.quote(target)} — service NOT registered after {_reload_budget}s of retries\" >> {shlex.quote(str(reload_log_path))}; "
             f"fi"
         )
         try:
@@ -3901,54 +3988,39 @@ def refresh_launchd_plist_if_needed() -> bool:
         )
         return True
 
-    # Bootout/bootstrap so launchd picks up the new definition. Retry the
-    # bootstrap on transient failure — under load (high loadavg, launchd
-    # busy), bootstrap can return non-zero even though bootout already tore
-    # down the prior registration, leaving the service orphan from KeepAlive
-    # supervision. Mirrors the retry+verify+log contract of the detached
-    # helper above. See hermes-restart rootcause handoff (2026-06-26).
+    # Bootout/bootstrap so launchd picks up the new definition. The reported
+    # incident (2026-06-26) happened when bootout succeeded but bootstrap
+    # failed silently under load (loadavg 9.48) during a graceful /restart
+    # drain, leaving the service unregistered — KeepAlive can't revive a job
+    # launchd no longer knows about. Retry the bootstrap (via the shared
+    # _launchctl_bootstrap EIO-recovery helper) until the label is actually
+    # registered or the drain window elapses, verify with `launchctl list`,
+    # and log exhaustion so the reload watchdog can detect a persistent orphan.
     subprocess.run(
         ["launchctl", "bootout", target],
         check=False,
         timeout=90,
     )
-    _bootstrap_ok = False
-    for _attempt in range(1, 6):
-        try:
-            subprocess.run(
-                ["launchctl", "bootstrap", domain, str(plist_path)],
-                check=True,
-                timeout=30,
-            )
-            _bootstrap_ok = True
-            break
-        except subprocess.CalledProcessError as _e:
-            logger.warning(
-                "launchctl bootstrap attempt %d/5 failed (rc=%s) for %s%s",
-                _attempt,
-                _e.returncode,
-                target,
-                "; retrying in 2s" if _attempt < 5 else "; no retries left",
-            )
-            if _attempt < 5:
-                import time as _bootstrap_sleep
-
-                _bootstrap_sleep.sleep(2)
-    if not _bootstrap_ok:
-        _reload_log_path = get_hermes_home() / "logs" / "launchd-reload.log"
-        try:
-            _reload_log_path.parent.mkdir(parents=True, exist_ok=True)
-            from datetime import datetime as _dt
-
-            with _reload_log_path.open("a", encoding="utf-8") as _f:
-                _f.write(
-                    f"[{_dt.now().astimezone().strftime('%Y-%m-%d %H:%M:%S %z')}] "
-                    f"FAILED launchd reload of {target} — bootstrap did not "
-                    f"succeed after 5 attempts (refresh ran outside gateway "
-                    f"process tree)\n"
-                )
-        except OSError:
-            pass
+    # Size the retry window to the restart drain timeout (default 180s), not a
+    # fixed ~10s: the failure mode occurs while the old gateway is still
+    # draining, so a short window can exhaust before launchd settles.
+    _reload_budget = max(30.0, _get_restart_drain_timeout())
+    _deadline = time.monotonic() + _reload_budget
+    if not _retry_launchctl_bootstrap_until_registered(
+        domain, plist_path, label, deadline=_deadline
+    ):
+        _append_launchd_reload_log(
+            f"FAILED launchd reload of {target} — service NOT registered after "
+            f"retrying for {int(_reload_budget)}s (refresh ran outside gateway "
+            f"process tree)"
+        )
+        logger.error(
+            "launchd reload of %s failed — service not registered after %ds of "
+            "retries; see %s",
+            target,
+            int(_reload_budget),
+            _launchd_reload_log_path(),
+        )
     print(
         "↻ Updated gateway launchd service definition to match the current Hermes install"
     )
diff --git a/tests/hermes_cli/test_gateway_service.py b/tests/hermes_cli/test_gateway_service.py
index 487be7497..9ac0baf5f 100644
--- a/tests/hermes_cli/test_gateway_service.py
+++ b/tests/hermes_cli/test_gateway_service.py
@@ -3469,3 +3469,82 @@ class TestLaunchctlBootstrapEioRetry:
         assert excinfo.value.returncode == 125
         # A non-EIO failure is not the already-loaded case: no bootout/retry.
         assert calls == [["launchctl", "bootstrap", self.DOMAIN, self.PLIST]]
+
+
+class TestRetryLaunchctlBootstrapUntilRegistered:
+    """`_retry_launchctl_bootstrap_until_registered` — salvage of #53277.
+
+    Covers the three review findings the salvage hardens: retry until the
+    label is actually LISTED (not just a zero bootstrap exit), TimeoutExpired
+    is retried (not escaped leaving the service unloaded), and the retry is
+    bounded by a wall-clock deadline rather than a fixed short window.
+    """
+
+    DOMAIN = "gui/501"
+    PLIST = "/tmp/ai.hermes.gateway.plist"
+    LABEL = "ai.hermes.gateway"
+
+    def test_returns_true_once_label_is_registered(self, monkeypatch):
+        """Success requires launchctl list to confirm registration, not just
+        a zero bootstrap exit."""
+        list_results = iter([1, 0])  # first check: not registered, second: registered
+
+        def fake_run(cmd, check=False, **kwargs):
+            if cmd[:2] == ["launchctl", "list"]:
+                return SimpleNamespace(returncode=next(list_results))
+            return SimpleNamespace(returncode=0, stdout="", stderr="")
+
+        monkeypatch.setattr(gateway_cli.subprocess, "run", fake_run)
+        monkeypatch.setattr(gateway_cli.time, "sleep", lambda *_a, **_k: None)
+
+        ok = gateway_cli._retry_launchctl_bootstrap_until_registered(
+            self.DOMAIN, self.PLIST, self.LABEL,
+            deadline=gateway_cli.time.monotonic() + 60,
+        )
+        assert ok is True
+
+    def test_timeout_expired_is_retried_not_escaped(self, monkeypatch):
+        """A bootstrap that times out must be retried — it leaves the service
+        unloaded, so it must not escape the retry/log path (finding #2)."""
+        attempts = {"bootstrap": 0}
+
+        def fake_run(cmd, check=False, **kwargs):
+            if cmd[1] == "bootstrap":
+                attempts["bootstrap"] += 1
+                if attempts["bootstrap"] == 1:
+                    raise subprocess.TimeoutExpired(cmd, kwargs.get("timeout", 30))
+                return SimpleNamespace(returncode=0, stdout="", stderr="")
+            if cmd[:2] == ["launchctl", "list"]:
+                # registered only after the second (successful) bootstrap
+                return SimpleNamespace(returncode=0 if attempts["bootstrap"] >= 2 else 1)
+            return SimpleNamespace(returncode=0, stdout="", stderr="")
+
+        monkeypatch.setattr(gateway_cli.subprocess, "run", fake_run)
+        monkeypatch.setattr(gateway_cli.time, "sleep", lambda *_a, **_k: None)
+
+        ok = gateway_cli._retry_launchctl_bootstrap_until_registered(
+            self.DOMAIN, self.PLIST, self.LABEL,
+            deadline=gateway_cli.time.monotonic() + 60,
+        )
+        assert ok is True
+        assert attempts["bootstrap"] >= 2  # the timeout was retried, not raised
+
+    def test_returns_false_when_deadline_exhausts(self, monkeypatch):
+        """When the label never registers, the loop stops at the deadline and
+        returns False (so the caller logs the persistent orphan)."""
+        def fake_run(cmd, check=False, **kwargs):
+            if cmd[:2] == ["launchctl", "list"]:
+                return SimpleNamespace(returncode=1)  # never registered
+            if cmd[1] == "bootstrap":
+                raise subprocess.CalledProcessError(1, cmd)
+            return SimpleNamespace(returncode=0, stdout="", stderr="")
+
+        monkeypatch.setattr(gateway_cli.subprocess, "run", fake_run)
+        monkeypatch.setattr(gateway_cli.time, "sleep", lambda *_a, **_k: None)
+
+        # Deadline already in the past → exactly one attempt, then give up.
+        ok = gateway_cli._retry_launchctl_bootstrap_until_registered(
+            self.DOMAIN, self.PLIST, self.LABEL,
+            deadline=gateway_cli.time.monotonic() - 1,
+        )
+        assert ok is False