diff --git a/cli-config.yaml.example b/cli-config.yaml.example
index a0a2d7d8a1..5807cef7aa 100644
--- a/cli-config.yaml.example
+++ b/cli-config.yaml.example
@@ -480,6 +480,12 @@ agent:
   # Fires once per run when inactivity reaches this threshold (seconds).
   # Set to 0 to disable the warning.
   # gateway_timeout_warning: 900
+
+  # Graceful drain timeout for gateway stop/restart (seconds).
+  # The gateway stops accepting new work, waits for in-flight agents to
+  # finish, then interrupts anything still running after this timeout.
+  # 0 = no drain, interrupt immediately.
+  # restart_drain_timeout: 60
   
   # Enable verbose logging
   verbose: false
diff --git a/gateway/platforms/base.py b/gateway/platforms/base.py
index dfc06ef7cb..34aacc7a39 100644
--- a/gateway/platforms/base.py
+++ b/gateway/platforms/base.py
@@ -727,6 +727,7 @@ class BasePlatformAdapter(ABC):
         # working on a task after --replace or manual restarts.
         self._background_tasks: set[asyncio.Task] = set()
         self._expected_cancelled_tasks: set[asyncio.Task] = set()
+        self._busy_session_handler: Optional[Callable[[MessageEvent, str], Awaitable[bool]]] = None
         # Chats where auto-TTS on voice input is disabled (set by /voice off)
         self._auto_tts_disabled_chats: set = set()
         # Chats where typing indicator is paused (e.g. during approval waits).
@@ -815,6 +816,10 @@ class BasePlatformAdapter(ABC):
         an optional response string.
         """
         self._message_handler = handler
+
+    def set_busy_session_handler(self, handler: Optional[Callable[[MessageEvent, str], Awaitable[bool]]]) -> None:
+        """Set an optional handler for messages arriving during active sessions."""
+        self._busy_session_handler = handler
     
     def set_session_store(self, session_store: Any) -> None:
         """
@@ -1396,7 +1401,7 @@ class BasePlatformAdapter(ABC):
             # session lifecycle and its cleanup races with the running task
             # (see PR #4926).
             cmd = event.get_command()
-            if cmd in ("approve", "deny", "status", "stop", "new", "reset", "background"):
+            if cmd in ("approve", "deny", "status", "stop", "new", "reset", "background", "restart"):
                 logger.debug(
                     "[%s] Command '/%s' bypassing active-session guard for %s",
                     self.name, cmd, session_key,
@@ -1415,6 +1420,13 @@ class BasePlatformAdapter(ABC):
                     logger.error("[%s] Command '/%s' dispatch failed: %s", self.name, cmd, e, exc_info=True)
                 return
 
+            if self._busy_session_handler is not None:
+                try:
+                    if await self._busy_session_handler(event, session_key):
+                        return
+                except Exception as e:
+                    logger.error("[%s] Busy-session handler failed: %s", self.name, e, exc_info=True)
+
             # Special case: photo bursts/albums frequently arrive as multiple near-
             # simultaneous messages. Queue them without interrupting the active run,
             # then process them immediately after the current task finishes.
diff --git a/gateway/run.py b/gateway/run.py
index 0dff622ae8..e4caedd9e4 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -186,6 +186,12 @@ if _config_path.exists():
                 os.environ["HERMES_AGENT_TIMEOUT"] = str(_agent_cfg["gateway_timeout"])
             if "gateway_timeout_warning" in _agent_cfg and "HERMES_AGENT_TIMEOUT_WARNING" not in os.environ:
                 os.environ["HERMES_AGENT_TIMEOUT_WARNING"] = str(_agent_cfg["gateway_timeout_warning"])
+            if "restart_drain_timeout" in _agent_cfg and "HERMES_RESTART_DRAIN_TIMEOUT" not in os.environ:
+                os.environ["HERMES_RESTART_DRAIN_TIMEOUT"] = str(_agent_cfg["restart_drain_timeout"])
+        _display_cfg = _cfg.get("display", {})
+        if _display_cfg and isinstance(_display_cfg, dict):
+            if "busy_input_mode" in _display_cfg and "HERMES_GATEWAY_BUSY_INPUT_MODE" not in os.environ:
+                os.environ["HERMES_GATEWAY_BUSY_INPUT_MODE"] = str(_display_cfg["busy_input_mode"])
         # Timezone: bridge config.yaml → HERMES_TIMEZONE env var.
         # HERMES_TIMEZONE from .env takes precedence (already in os.environ).
         _tz_cfg = _cfg.get("timezone", "")
@@ -483,6 +489,8 @@ class GatewayRunner:
         self._reasoning_config = self._load_reasoning_config()
         self._service_tier = self._load_service_tier()
         self._show_reasoning = self._load_show_reasoning()
+        self._busy_input_mode = self._load_busy_input_mode()
+        self._restart_drain_timeout = self._load_restart_drain_timeout()
         self._provider_routing = self._load_provider_routing()
         self._fallback_model = self._load_fallback_model()
         self._smart_model_routing = self._load_smart_model_routing()
@@ -499,6 +507,13 @@ class GatewayRunner:
         self._exit_cleanly = False
         self._exit_with_failure = False
         self._exit_reason: Optional[str] = None
+        self._exit_code: Optional[int] = None
+        self._draining = False
+        self._restart_requested = False
+        self._restart_task_started = False
+        self._restart_detached = False
+        self._restart_via_service = False
+        self._stop_task: Optional[asyncio.Task] = None
         
         # Track running agents per session for interrupt support
         # Key: session_key, Value: AIAgent instance
@@ -759,6 +774,10 @@ class GatewayRunner:
     def exit_reason(self) -> Optional[str]:
         return self._exit_reason
 
+    @property
+    def exit_code(self) -> Optional[int]:
+        return self._exit_code
+
     def _session_key_for_source(self, source: SessionSource) -> str:
         """Resolve the current session key for a source, honoring gateway config when available."""
         if hasattr(self, "session_store") and self.session_store is not None:
@@ -868,6 +887,30 @@ class GatewayRunner:
         self._exit_cleanly = True
         self._exit_reason = reason
         self._shutdown_event.set()
+
+    def _running_agent_count(self) -> int:
+        return len(self._running_agents)
+
+    def _status_action_label(self) -> str:
+        return "restart" if self._restart_requested else "shutdown"
+
+    def _status_action_gerund(self) -> str:
+        return "restarting" if self._restart_requested else "shutting down"
+
+    def _queue_during_drain_enabled(self) -> bool:
+        return self._restart_requested and self._busy_input_mode == "queue"
+
+    def _update_runtime_status(self, gateway_state: Optional[str] = None, exit_reason: Optional[str] = None) -> None:
+        try:
+            from gateway.status import write_runtime_status
+            write_runtime_status(
+                gateway_state=gateway_state,
+                exit_reason=exit_reason,
+                restart_requested=self._restart_requested,
+                active_agents=self._running_agent_count(),
+            )
+        except Exception:
+            pass
     
     @staticmethod
     def _load_prefill_messages() -> List[Dict[str, Any]]:
@@ -994,6 +1037,43 @@ class GatewayRunner:
             pass
         return False
 
+    @staticmethod
+    def _load_busy_input_mode() -> str:
+        """Load gateway drain-time busy-input behavior from config/env."""
+        mode = os.getenv("HERMES_GATEWAY_BUSY_INPUT_MODE", "").strip().lower()
+        if not mode:
+            try:
+                import yaml as _y
+                cfg_path = _hermes_home / "config.yaml"
+                if cfg_path.exists():
+                    with open(cfg_path, encoding="utf-8") as _f:
+                        cfg = _y.safe_load(_f) or {}
+                    mode = str(cfg.get("display", {}).get("busy_input_mode", "") or "").strip().lower()
+            except Exception:
+                pass
+        return "queue" if mode == "queue" else "interrupt"
+
+    @staticmethod
+    def _load_restart_drain_timeout() -> float:
+        """Load graceful gateway restart/stop drain timeout in seconds."""
+        raw = os.getenv("HERMES_RESTART_DRAIN_TIMEOUT", "").strip()
+        if not raw:
+            try:
+                import yaml as _y
+                cfg_path = _hermes_home / "config.yaml"
+                if cfg_path.exists():
+                    with open(cfg_path, encoding="utf-8") as _f:
+                        cfg = _y.safe_load(_f) or {}
+                    raw = str(cfg.get("agent", {}).get("restart_drain_timeout", "") or "").strip()
+            except Exception:
+                pass
+        try:
+            value = float(raw) if raw else 60.0
+        except ValueError:
+            logger.warning("Invalid restart_drain_timeout '%s', using default 60s", raw)
+            return 60.0
+        return max(0.0, value)
+
     @staticmethod
     def _load_background_notifications_mode() -> str:
         """Load background process notification mode from config or env var.
@@ -1078,6 +1158,142 @@ class GatewayRunner:
             pass
         return {}
 
+    def _snapshot_running_agents(self) -> Dict[str, Any]:
+        return {
+            session_key: agent
+            for session_key, agent in self._running_agents.items()
+            if agent is not _AGENT_PENDING_SENTINEL
+        }
+
+    def _queue_or_replace_pending_event(self, session_key: str, event: MessageEvent) -> None:
+        adapter = self.adapters.get(event.source.platform)
+        if not adapter:
+            return
+        existing = adapter._pending_messages.get(session_key)
+        if existing and getattr(existing, "message_type", None) == MessageType.PHOTO and event.message_type == MessageType.PHOTO:
+            existing.media_urls.extend(event.media_urls)
+            existing.media_types.extend(event.media_types)
+            if event.text:
+                existing.text = BasePlatformAdapter._merge_caption(existing.text, event.text)
+            return
+        adapter._pending_messages[session_key] = event
+
+    async def _handle_active_session_busy_message(self, event: MessageEvent, session_key: str) -> bool:
+        if not self._draining:
+            return False
+
+        adapter = self.adapters.get(event.source.platform)
+        if not adapter:
+            return True
+
+        thread_meta = {"thread_id": event.source.thread_id} if event.source.thread_id else None
+        if self._queue_during_drain_enabled():
+            self._queue_or_replace_pending_event(session_key, event)
+            message = f"⏳ Gateway {self._status_action_gerund()} — queued for the next turn after it comes back."
+        else:
+            message = f"⏳ Gateway is {self._status_action_gerund()} and is not accepting another turn right now."
+
+        await adapter._send_with_retry(
+            chat_id=event.source.chat_id,
+            content=message,
+            reply_to=event.message_id,
+            metadata=thread_meta,
+        )
+        return True
+
+    async def _drain_active_agents(self, timeout: float) -> tuple[Dict[str, Any], bool]:
+        snapshot = self._snapshot_running_agents()
+        if not self._running_agents:
+            self._update_runtime_status("draining")
+            return snapshot, False
+
+        self._update_runtime_status("draining")
+        if timeout <= 0:
+            return snapshot, True
+
+        deadline = asyncio.get_running_loop().time() + timeout
+        while self._running_agents and asyncio.get_running_loop().time() < deadline:
+            self._update_runtime_status("draining")
+            await asyncio.sleep(0.1)
+        timed_out = bool(self._running_agents)
+        self._update_runtime_status("draining")
+        return snapshot, timed_out
+
+    def _interrupt_running_agents(self, reason: str) -> None:
+        for session_key, agent in list(self._running_agents.items()):
+            if agent is _AGENT_PENDING_SENTINEL:
+                continue
+            try:
+                agent.interrupt(reason)
+                logger.debug("Interrupted running agent for session %s during shutdown", session_key[:20])
+            except Exception as e:
+                logger.debug("Failed interrupting agent during shutdown: %s", e)
+
+    def _finalize_shutdown_agents(self, active_agents: Dict[str, Any]) -> None:
+        for agent in active_agents.values():
+            try:
+                from hermes_cli.plugins import invoke_hook as _invoke_hook
+                _invoke_hook(
+                    "on_session_finalize",
+                    session_id=getattr(agent, "session_id", None),
+                    platform="gateway",
+                )
+            except Exception:
+                pass
+            try:
+                if hasattr(agent, "shutdown_memory_provider"):
+                    agent.shutdown_memory_provider()
+            except Exception:
+                pass
+
+    async def _launch_detached_restart_command(self) -> None:
+        import shutil
+        import subprocess
+
+        hermes_cmd = _resolve_hermes_bin()
+        if not hermes_cmd:
+            logger.error("Could not locate hermes binary for detached /restart")
+            return
+
+        current_pid = os.getpid()
+        cmd = " ".join(shlex.quote(part) for part in hermes_cmd)
+        shell_cmd = (
+            f"while kill -0 {current_pid} 2>/dev/null; do sleep 0.2; done; "
+            f"{cmd} gateway restart"
+        )
+        setsid_bin = shutil.which("setsid")
+        if setsid_bin:
+            subprocess.Popen(
+                [setsid_bin, "bash", "-lc", shell_cmd],
+                stdout=subprocess.DEVNULL,
+                stderr=subprocess.DEVNULL,
+                start_new_session=True,
+            )
+        else:
+            subprocess.Popen(
+                ["bash", "-lc", shell_cmd],
+                stdout=subprocess.DEVNULL,
+                stderr=subprocess.DEVNULL,
+                start_new_session=True,
+            )
+
+    def request_restart(self, *, detached: bool = False, via_service: bool = False) -> bool:
+        if self._restart_task_started:
+            return False
+        self._restart_requested = True
+        self._restart_detached = detached
+        self._restart_via_service = via_service
+        self._restart_task_started = True
+
+        async def _run_restart() -> None:
+            await asyncio.sleep(0.05)
+            await self.stop(restart=True, detached_restart=detached, service_restart=via_service)
+
+        task = asyncio.create_task(_run_restart())
+        self._background_tasks.add(task)
+        task.add_done_callback(self._background_tasks.discard)
+        return True
+
     async def start(self) -> bool:
         """
         Start the gateway and all configured platform adapters.
@@ -1165,6 +1381,7 @@ class GatewayRunner:
             adapter.set_message_handler(self._handle_message)
             adapter.set_fatal_error_handler(self._handle_adapter_fatal_error)
             adapter.set_session_store(self.session_store)
+            adapter.set_busy_session_handler(self._handle_active_session_busy_message)
             
             # Try to connect
             logger.info("Connecting to %s...", platform.value)
@@ -1240,11 +1457,7 @@ class GatewayRunner:
         self.delivery_router.adapters = self.adapters
         
         self._running = True
-        try:
-            from gateway.status import write_runtime_status
-            write_runtime_status(gateway_state="running", exit_reason=None)
-        except Exception:
-            pass
+        self._update_runtime_status("running")
         
         # Emit gateway:startup hook
         hook_count = len(self.hooks.loaded_hooks)
@@ -1479,6 +1692,7 @@ class GatewayRunner:
                     adapter.set_message_handler(self._handle_message)
                     adapter.set_fatal_error_handler(self._handle_adapter_fatal_error)
                     adapter.set_session_store(self.session_store)
+                    adapter.set_busy_session_handler(self._handle_active_session_busy_message)
 
                     success = await adapter.connect()
                     if success:
@@ -1525,90 +1739,108 @@ class GatewayRunner:
                     return
                 await asyncio.sleep(1)
 
-    async def stop(self) -> None:
+    async def stop(
+        self,
+        *,
+        restart: bool = False,
+        detached_restart: bool = False,
+        service_restart: bool = False,
+    ) -> None:
         """Stop the gateway and disconnect all adapters."""
-        logger.info("Stopping gateway...")
-        self._running = False
+        if restart:
+            self._restart_requested = True
+            self._restart_detached = detached_restart
+            self._restart_via_service = service_restart
+        if self._stop_task is not None:
+            await self._stop_task
+            return
 
-        for session_key, agent in list(self._running_agents.items()):
-            if agent is _AGENT_PENDING_SENTINEL:
-                continue
+        async def _stop_impl() -> None:
+            logger.info(
+                "Stopping gateway%s...",
+                " for restart" if self._restart_requested else "",
+            )
+            self._running = False
+            self._draining = True
+
+            timeout = self._restart_drain_timeout
+            active_agents, timed_out = await self._drain_active_agents(timeout)
+            if timed_out:
+                logger.warning(
+                    "Gateway drain timed out after %.1fs with %d active agent(s); interrupting remaining work.",
+                    timeout,
+                    self._running_agent_count(),
+                )
+                self._interrupt_running_agents(
+                    "Gateway restarting" if self._restart_requested else "Gateway shutting down"
+                )
+                interrupt_deadline = asyncio.get_running_loop().time() + 5.0
+                while self._running_agents and asyncio.get_running_loop().time() < interrupt_deadline:
+                    self._update_runtime_status("draining")
+                    await asyncio.sleep(0.1)
+
+            if self._restart_requested and self._restart_detached:
+                try:
+                    await self._launch_detached_restart_command()
+                except Exception as e:
+                    logger.error("Failed to launch detached gateway restart: %s", e)
+
+            self._finalize_shutdown_agents(active_agents)
+
+            for platform, adapter in list(self.adapters.items()):
+                try:
+                    await adapter.cancel_background_tasks()
+                except Exception as e:
+                    logger.debug("✗ %s background-task cancel error: %s", platform.value, e)
+                try:
+                    await adapter.disconnect()
+                    logger.info("✓ %s disconnected", platform.value)
+                except Exception as e:
+                    logger.error("✗ %s disconnect error: %s", platform.value, e)
+
+            for _task in list(self._background_tasks):
+                if _task is self._stop_task:
+                    continue
+                _task.cancel()
+            self._background_tasks.clear()
+
+            self.adapters.clear()
+            self._running_agents.clear()
+            self._pending_messages.clear()
+            self._pending_approvals.clear()
+            self._shutdown_event.set()
+
+            # Global cleanup: kill any remaining tool subprocesses not tied
+            # to a specific agent (catch-all for zombie prevention).
             try:
-                agent.interrupt("Gateway shutting down")
-                logger.debug("Interrupted running agent for session %s during shutdown", session_key[:20])
-            except Exception as e:
-                logger.debug("Failed interrupting agent during shutdown: %s", e)
-            # Fire plugin on_session_finalize hook before memory shutdown
-            try:
-                from hermes_cli.plugins import invoke_hook as _invoke_hook
-                _invoke_hook("on_session_finalize",
-                             session_id=getattr(agent, 'session_id', None),
-                             platform="gateway")
+                from tools.process_registry import process_registry
+                process_registry.kill_all()
             except Exception:
                 pass
-            # Shut down memory provider at actual session boundary
             try:
-                if hasattr(agent, 'shutdown_memory_provider'):
-                    agent.shutdown_memory_provider()
+                from tools.terminal_tool import cleanup_all_environments
+                cleanup_all_environments()
             except Exception:
                 pass
-            # Close tool resources (terminal sandboxes, browser daemons,
-            # background processes, httpx clients) to prevent zombie
-            # process accumulation.
             try:
-                if hasattr(agent, 'close'):
-                    agent.close()
+                from tools.browser_tool import cleanup_all_browsers
+                cleanup_all_browsers()
             except Exception:
                 pass
 
-        for platform, adapter in list(self.adapters.items()):
-            try:
-                await adapter.cancel_background_tasks()
-            except Exception as e:
-                logger.debug("✗ %s background-task cancel error: %s", platform.value, e)
-            try:
-                await adapter.disconnect()
-                logger.info("✓ %s disconnected", platform.value)
-            except Exception as e:
-                logger.error("✗ %s disconnect error: %s", platform.value, e)
+            from gateway.status import remove_pid_file
+            remove_pid_file()
 
-        # Cancel any pending background tasks
-        for _task in list(self._background_tasks):
-            _task.cancel()
-        self._background_tasks.clear()
+            if self._restart_requested and self._restart_via_service:
+                self._exit_code = 75
+                self._exit_reason = self._exit_reason or "Gateway restart requested"
 
-        self.adapters.clear()
-        self._running_agents.clear()
-        self._pending_messages.clear()
-        self._pending_approvals.clear()
-        self._shutdown_event.set()
+            self._draining = False
+            self._update_runtime_status("stopped", self._exit_reason)
+            logger.info("Gateway stopped")
 
-        # Global cleanup: kill any remaining tool subprocesses not tied
-        # to a specific agent (catch-all for zombie prevention).
-        try:
-            from tools.process_registry import process_registry
-            process_registry.kill_all()
-        except Exception:
-            pass
-        try:
-            from tools.terminal_tool import cleanup_all_environments
-            cleanup_all_environments()
-        except Exception:
-            pass
-        try:
-            from tools.browser_tool import cleanup_all_browsers
-            cleanup_all_browsers()
-        except Exception:
-            pass
-
-        from gateway.status import remove_pid_file, write_runtime_status
-        remove_pid_file()
-        try:
-            write_runtime_status(gateway_state="stopped", exit_reason=self._exit_reason)
-        except Exception:
-            pass
-        
-        logger.info("Gateway stopped")
+        self._stop_task = asyncio.create_task(_stop_impl())
+        await self._stop_task
     
     async def wait_for_shutdown(self) -> None:
         """Wait for shutdown signal."""
@@ -2014,6 +2246,9 @@ class GatewayRunner:
             _evt_cmd = event.get_command()
             _cmd_def_inner = _resolve_cmd_inner(_evt_cmd) if _evt_cmd else None
 
+            if _cmd_def_inner and _cmd_def_inner.name == "restart":
+                return await self._handle_restart_command(event)
+
             # /stop must hard-kill the session when an agent is running.
             # A soft interrupt (agent.interrupt()) doesn't help when the agent
             # is truly hung — the executor thread is blocked and never checks
@@ -2123,6 +2358,14 @@ class GatewayRunner:
                 if adapter:
                     adapter._pending_messages[_quick_key] = event
                 return None
+            if self._draining:
+                if self._queue_during_drain_enabled():
+                    self._queue_or_replace_pending_event(_quick_key, event)
+                return (
+                    f"⏳ Gateway {self._status_action_gerund()} — queued for the next turn after it comes back."
+                    if self._queue_during_drain_enabled()
+                    else f"⏳ Gateway is {self._status_action_gerund()} and is not accepting another turn right now."
+                )
             logger.debug("PRIORITY interrupt for session %s", _quick_key[:20])
             running_agent.interrupt(event.text)
             if _quick_key in self._pending_messages:
@@ -2164,6 +2407,9 @@ class GatewayRunner:
 
         if canonical == "status":
             return await self._handle_status_command(event)
+
+        if canonical == "restart":
+            return await self._handle_restart_command(event)
         
         if canonical == "stop":
             return await self._handle_stop_command(event)
@@ -2262,6 +2508,9 @@ class GatewayRunner:
         if canonical == "voice":
             return await self._handle_voice_command(event)
 
+        if self._draining:
+            return f"⏳ Gateway is {self._status_action_gerund()} and is not accepting new work right now."
+
         # User-defined quick commands (bypass agent loop, no LLM call)
         if command:
             if isinstance(self.config, dict):
@@ -3556,7 +3805,21 @@ class GatewayRunner:
             return "⚡ Force-stopped. The session is unlocked — you can send a new message."
         else:
             return "No active task to stop."
-    
+
+    async def _handle_restart_command(self, event: MessageEvent) -> str:
+        """Handle /restart command - drain active work, then restart the gateway."""
+        if self._restart_requested or self._draining:
+            count = self._running_agent_count()
+            if count:
+                return f"⏳ Draining {count} active agent(s) before restart..."
+            return "⏳ Gateway restart already in progress..."
+
+        active_agents = self._running_agent_count()
+        self.request_restart(detached=True, via_service=False)
+        if active_agents:
+            return f"⏳ Draining {active_agents} active agent(s) before restart..."
+        return "♻ Restarting gateway..."
+
     async def _handle_help_command(self, event: MessageEvent) -> str:
         """Handle /help command - list available commands."""
         from hermes_cli.commands import gateway_help_lines
@@ -7375,6 +7638,8 @@ class GatewayRunner:
                 await asyncio.sleep(0.05)
             if session_key:
                 self._running_agents[session_key] = agent_holder[0]
+                if self._draining:
+                    self._update_runtime_status("draining")
         
         tracking_task = asyncio.create_task(track_agent())
         
@@ -7627,6 +7892,14 @@ class GatewayRunner:
                     except Exception:
                         pass
 
+            if self._draining and pending:
+                logger.info(
+                    "Discarding pending follow-up for session %s during gateway %s",
+                    session_key[:20] if session_key else "?",
+                    self._status_action_label(),
+                )
+                pending = None
+
             if pending:
                 logger.debug("Processing pending message: '%s...'", pending[:40])
                 
@@ -7703,6 +7976,8 @@ class GatewayRunner:
                 del self._running_agents[session_key]
             if session_key:
                 self._running_agents_ts.pop(session_key, None)
+            if self._draining:
+                self._update_runtime_status("draining")
             
             # Wait for cancelled tasks
             for task in [progress_task, interrupt_monitor, tracking_task, _notify_task]:
@@ -7900,13 +8175,21 @@ async def start_gateway(config: Optional[GatewayConfig] = None, replace: bool =
     runner = GatewayRunner(config)
     
     # Set up signal handlers
-    def signal_handler():
+    def shutdown_signal_handler():
         asyncio.create_task(runner.stop())
+
+    def restart_signal_handler():
+        runner.request_restart(detached=False, via_service=True)
     
     loop = asyncio.get_event_loop()
     for sig in (signal.SIGINT, signal.SIGTERM):
         try:
-            loop.add_signal_handler(sig, signal_handler)
+            loop.add_signal_handler(sig, shutdown_signal_handler)
+        except NotImplementedError:
+            pass
+    if hasattr(signal, "SIGUSR1"):
+        try:
+            loop.add_signal_handler(signal.SIGUSR1, restart_signal_handler)
         except NotImplementedError:
             pass
     
@@ -7956,6 +8239,9 @@ async def start_gateway(config: Optional[GatewayConfig] = None, replace: bool =
     except Exception:
         pass
 
+    if runner.exit_code is not None:
+        raise SystemExit(runner.exit_code)
+
     return True
 
 
diff --git a/gateway/status.py b/gateway/status.py
index ff91262061..5423461c2f 100644
--- a/gateway/status.py
+++ b/gateway/status.py
@@ -158,6 +158,8 @@ def _build_runtime_status_record() -> dict[str, Any]:
     payload.update({
         "gateway_state": "starting",
         "exit_reason": None,
+        "restart_requested": False,
+        "active_agents": 0,
         "platforms": {},
         "updated_at": _utc_now_iso(),
     })
@@ -218,6 +220,8 @@ def write_runtime_status(
     *,
     gateway_state: Optional[str] = None,
     exit_reason: Optional[str] = None,
+    restart_requested: Optional[bool] = None,
+    active_agents: Optional[int] = None,
     platform: Optional[str] = None,
     platform_state: Optional[str] = None,
     error_code: Optional[str] = None,
@@ -236,6 +240,10 @@ def write_runtime_status(
         payload["gateway_state"] = gateway_state
     if exit_reason is not None:
         payload["exit_reason"] = exit_reason
+    if restart_requested is not None:
+        payload["restart_requested"] = bool(restart_requested)
+    if active_agents is not None:
+        payload["active_agents"] = max(0, int(active_agents))
 
     if platform is not None:
         platform_payload = payload["platforms"].get(platform, {})
diff --git a/hermes_cli/commands.py b/hermes_cli/commands.py
index 84ec873a37..7cf8f30527 100644
--- a/hermes_cli/commands.py
+++ b/hermes_cli/commands.py
@@ -140,6 +140,8 @@ COMMAND_REGISTRY: list[CommandDef] = [
     CommandDef("commands", "Browse all commands and skills (paginated)", "Info",
                gateway_only=True, args_hint="[page]"),
     CommandDef("help", "Show available commands", "Info"),
+    CommandDef("restart", "Gracefully restart the gateway after draining active runs", "Info",
+               gateway_only=True),
     CommandDef("usage", "Show token usage and rate limits for the current session", "Info"),
     CommandDef("insights", "Show usage insights and analytics", "Info",
                args_hint="[days]"),
diff --git a/hermes_cli/config.py b/hermes_cli/config.py
index 5ddf37d082..2cb6a8d62a 100644
--- a/hermes_cli/config.py
+++ b/hermes_cli/config.py
@@ -269,6 +269,11 @@ DEFAULT_CONFIG = {
         # tools or receiving API responses.  Only fires when the agent has
         # been completely idle for this duration.  0 = unlimited.
         "gateway_timeout": 1800,
+        # Graceful drain timeout for gateway stop/restart (seconds).
+        # The gateway stops accepting new work, waits for running agents
+        # to finish, then interrupts any remaining runs after the timeout.
+        # 0 = no drain, interrupt immediately.
+        "restart_drain_timeout": 60,
         "service_tier": "",
         # Tool-use enforcement: injects system prompt guidance that tells the
         # model to actually call tools instead of describing intended actions.
diff --git a/hermes_cli/gateway.py b/hermes_cli/gateway.py
index 58029c888a..0f5f4d15ff 100644
--- a/hermes_cli/gateway.py
+++ b/hermes_cli/gateway.py
@@ -15,7 +15,15 @@ from pathlib import Path
 PROJECT_ROOT = Path(__file__).parent.parent.resolve()
 
 from gateway.status import terminate_pid
-from hermes_cli.config import get_env_value, get_hermes_home, save_env_value, is_managed, managed_error
+from hermes_cli.config import (
+    DEFAULT_CONFIG,
+    get_env_value,
+    get_hermes_home,
+    is_managed,
+    managed_error,
+    read_raw_config,
+    save_env_value,
+)
 # display_hermes_home is imported lazily at call sites to avoid ImportError
 # when hermes_constants is cached from a pre-update version during `hermes update`.
 from hermes_cli.setup import (
@@ -687,6 +695,7 @@ def generate_systemd_unit(system: bool = False, run_as_user: str | None = None)
             path_entries.append(resolved_node_dir)
 
     common_bin_paths = ["/usr/local/sbin", "/usr/local/bin", "/usr/sbin", "/usr/bin", "/sbin", "/bin"]
+    restart_timeout = max(60, int(_get_restart_drain_timeout() or 0))
 
     if system:
         username, group_name, home_dir = _system_service_identity(run_as_user)
@@ -725,9 +734,11 @@ Environment="VIRTUAL_ENV={venv_dir}"
 Environment="HERMES_HOME={hermes_home}"
 Restart=on-failure
 RestartSec=30
+RestartForceExitStatus=75
 KillMode=mixed
 KillSignal=SIGTERM
-TimeoutStopSec=60
+ExecReload=/bin/kill -USR1 $MAINPID
+TimeoutStopSec={restart_timeout}
 StandardOutput=journal
 StandardError=journal
 
@@ -755,9 +766,11 @@ Environment="VIRTUAL_ENV={venv_dir}"
 Environment="HERMES_HOME={hermes_home}"
 Restart=on-failure
 RestartSec=30
+RestartForceExitStatus=75
 KillMode=mixed
 KillSignal=SIGTERM
-TimeoutStopSec=60
+ExecReload=/bin/kill -USR1 $MAINPID
+TimeoutStopSec={restart_timeout}
 StandardOutput=journal
 StandardError=journal
 
@@ -860,6 +873,19 @@ def _select_systemd_scope(system: bool = False) -> bool:
     return get_systemd_unit_path(system=True).exists() and not get_systemd_unit_path(system=False).exists()
 
 
+def _get_restart_drain_timeout() -> float:
+    """Return the configured gateway restart drain timeout in seconds."""
+    raw = os.getenv("HERMES_RESTART_DRAIN_TIMEOUT", "").strip()
+    if not raw:
+        cfg = read_raw_config()
+        agent_cfg = cfg.get("agent", {}) if isinstance(cfg, dict) else {}
+        raw = str(agent_cfg.get("restart_drain_timeout", DEFAULT_CONFIG["agent"]["restart_drain_timeout"]))
+    try:
+        return max(0.0, float(raw))
+    except (TypeError, ValueError):
+        return float(DEFAULT_CONFIG["agent"]["restart_drain_timeout"])
+
+
 def systemd_install(force: bool = False, system: bool = False, run_as_user: str | None = None):
     if system:
         _require_root_for_system_service("install")
@@ -945,7 +971,7 @@ def systemd_restart(system: bool = False):
     if system:
         _require_root_for_system_service("restart")
     refresh_systemd_unit_if_needed(system=system)
-    subprocess.run(_systemctl_cmd(system) + ["restart", get_service_name()], check=True, timeout=90)
+    subprocess.run(_systemctl_cmd(system) + ["reload-or-restart", get_service_name()], check=True, timeout=90)
     print(f"✓ {_service_scope_label(system).capitalize()} service restarted")
 
 
@@ -1233,7 +1259,7 @@ def launchd_stop():
     _wait_for_gateway_exit(timeout=10.0, force_after=5.0)
     print("✓ Service stopped")
 
-def _wait_for_gateway_exit(timeout: float = 10.0, force_after: float = 5.0):
+def _wait_for_gateway_exit(timeout: float = 10.0, force_after: float | None = 5.0) -> bool:
     """Wait for the gateway process (by saved PID) to exit.
 
     Uses the PID from the gateway.pid file — not launchd labels — so this
@@ -1248,21 +1274,21 @@ def _wait_for_gateway_exit(timeout: float = 10.0, force_after: float = 5.0):
     from gateway.status import get_running_pid
 
     deadline = time.monotonic() + timeout
-    force_deadline = time.monotonic() + force_after
+    force_deadline = (time.monotonic() + force_after) if force_after is not None else None
     force_sent = False
 
     while time.monotonic() < deadline:
         pid = get_running_pid()
         if pid is None:
-            return  # Process exited cleanly.
+            return True  # Process exited cleanly.
 
-        if not force_sent and time.monotonic() >= force_deadline:
+        if force_after is not None and not force_sent and time.monotonic() >= force_deadline:
             # Grace period expired — force-kill the specific PID.
             try:
                 terminate_pid(pid, force=True)
                 print(f"⚠ Gateway PID {pid} did not exit gracefully; sent SIGKILL")
             except (ProcessLookupError, PermissionError, OSError):
-                return  # Already gone or we can't touch it.
+                return True  # Already gone or we can't touch it.
             force_sent = True
 
         time.sleep(0.3)
@@ -1271,15 +1297,27 @@ def _wait_for_gateway_exit(timeout: float = 10.0, force_after: float = 5.0):
     remaining_pid = get_running_pid()
     if remaining_pid is not None:
         print(f"⚠ Gateway PID {remaining_pid} still running after {timeout}s — restart may fail")
+        return False
+    return True
 
 
 def launchd_restart():
     label = get_launchd_label()
     target = f"{_launchd_domain()}/{label}"
-    # Use kickstart -k so launchd performs an atomic kill+restart.
-    # A two-step stop/start from inside the gateway's own process tree
-    # would kill the shell before the start command is reached.
+    drain_timeout = _get_restart_drain_timeout()
+    from gateway.status import get_running_pid
+
     try:
+        pid = get_running_pid()
+        if pid is not None:
+            try:
+                terminate_pid(pid, force=False)
+            except (ProcessLookupError, PermissionError, OSError):
+                pid = None
+            if pid is not None:
+                exited = _wait_for_gateway_exit(timeout=drain_timeout, force_after=None)
+                if not exited:
+                    print(f"⚠ Gateway drain timed out after {drain_timeout:.0f}s — forcing launchd restart")
         subprocess.run(["launchctl", "kickstart", "-k", target], check=True, timeout=90)
         print("✓ Service restarted")
     except subprocess.CalledProcessError as e:
@@ -1750,6 +1788,8 @@ def _runtime_health_lines() -> list[str]:
     lines: list[str] = []
     gateway_state = state.get("gateway_state")
     exit_reason = state.get("exit_reason")
+    active_agents = state.get("active_agents")
+    restart_requested = state.get("restart_requested")
     platforms = state.get("platforms", {}) or {}
 
     for platform, pdata in platforms.items():
@@ -1759,6 +1799,10 @@ def _runtime_health_lines() -> list[str]:
 
     if gateway_state == "startup_failed" and exit_reason:
         lines.append(f"⚠ Last startup issue: {exit_reason}")
+    elif gateway_state == "draining":
+        action = "restart" if restart_requested else "shutdown"
+        count = int(active_agents or 0)
+        lines.append(f"⏳ Gateway draining for {action} ({count} active agent(s))")
     elif gateway_state == "stopped" and exit_reason:
         lines.append(f"⚠ Last shutdown reason: {exit_reason}")
 
diff --git a/tests/gateway/test_gateway_shutdown.py b/tests/gateway/test_gateway_shutdown.py
index 439fbfdb05..b6a7f8fa72 100644
--- a/tests/gateway/test_gateway_shutdown.py
+++ b/tests/gateway/test_gateway_shutdown.py
@@ -37,6 +37,30 @@ def _source(chat_id="123456", chat_type="dm"):
     )
 
 
+def _make_runner() -> GatewayRunner:
+    runner = object.__new__(GatewayRunner)
+    runner.config = GatewayConfig(platforms={Platform.TELEGRAM: PlatformConfig(enabled=True, token="***")})
+    runner._running = True
+    runner._shutdown_event = asyncio.Event()
+    runner._exit_reason = None
+    runner._exit_code = None
+    runner._pending_messages = {}
+    runner._pending_approvals = {}
+    runner._background_tasks = set()
+    runner._running_agents = {}
+    runner._running_agents_ts = {}
+    runner._draining = False
+    runner._restart_requested = False
+    runner._restart_task_started = False
+    runner._restart_detached = False
+    runner._restart_via_service = False
+    runner._restart_drain_timeout = 60.0
+    runner._stop_task = None
+    runner._shutdown_all_gateway_honcho = lambda: None
+    runner._update_runtime_status = MagicMock()
+    return runner
+
+
 @pytest.mark.asyncio
 async def test_cancel_background_tasks_cancels_inflight_message_processing():
     adapter = StubAdapter()
@@ -65,15 +89,10 @@ async def test_cancel_background_tasks_cancels_inflight_message_processing():
 
 @pytest.mark.asyncio
 async def test_gateway_stop_interrupts_running_agents_and_cancels_adapter_tasks():
-    runner = object.__new__(GatewayRunner)
-    runner.config = GatewayConfig(platforms={Platform.TELEGRAM: PlatformConfig(enabled=True, token="***")})
-    runner._running = True
-    runner._shutdown_event = asyncio.Event()
-    runner._exit_reason = None
+    runner = _make_runner()
     runner._pending_messages = {"session": "pending text"}
     runner._pending_approvals = {"session": {"command": "rm -rf /tmp/x"}}
-    runner._background_tasks = set()
-    runner._shutdown_all_gateway_honcho = lambda: None
+    runner._restart_drain_timeout = 0.0
 
     adapter = StubAdapter()
     release = asyncio.Event()
@@ -105,3 +124,49 @@ async def test_gateway_stop_interrupts_running_agents_and_cancels_adapter_tasks(
     assert runner._pending_messages == {}
     assert runner._pending_approvals == {}
     assert runner._shutdown_event.is_set() is True
+
+
+@pytest.mark.asyncio
+async def test_gateway_stop_drains_running_agents_before_disconnect():
+    runner = _make_runner()
+    adapter = StubAdapter()
+    disconnect_mock = AsyncMock()
+    adapter.disconnect = disconnect_mock
+    runner.adapters = {Platform.TELEGRAM: adapter}
+
+    running_agent = MagicMock()
+    runner._running_agents = {"session": running_agent}
+
+    async def finish_agent():
+        await asyncio.sleep(0.05)
+        runner._running_agents.clear()
+
+    asyncio.create_task(finish_agent())
+
+    with patch("gateway.status.remove_pid_file"), patch("gateway.status.write_runtime_status"):
+        await runner.stop()
+
+    running_agent.interrupt.assert_not_called()
+    disconnect_mock.assert_awaited_once()
+    assert runner._shutdown_event.is_set() is True
+
+
+@pytest.mark.asyncio
+async def test_gateway_stop_interrupts_after_drain_timeout():
+    runner = _make_runner()
+    runner._restart_drain_timeout = 0.05
+
+    adapter = StubAdapter()
+    disconnect_mock = AsyncMock()
+    adapter.disconnect = disconnect_mock
+    runner.adapters = {Platform.TELEGRAM: adapter}
+
+    running_agent = MagicMock()
+    runner._running_agents = {"session": running_agent}
+
+    with patch("gateway.status.remove_pid_file"), patch("gateway.status.write_runtime_status"):
+        await runner.stop()
+
+    running_agent.interrupt.assert_called_once_with("Gateway shutting down")
+    disconnect_mock.assert_awaited_once()
+    assert runner._shutdown_event.is_set() is True
diff --git a/tests/gateway/test_restart_drain.py b/tests/gateway/test_restart_drain.py
new file mode 100644
index 0000000000..2c59f9a976
--- /dev/null
+++ b/tests/gateway/test_restart_drain.py
@@ -0,0 +1,133 @@
+import asyncio
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+
+from gateway.config import GatewayConfig, Platform, PlatformConfig
+from gateway.platforms.base import BasePlatformAdapter, MessageEvent, MessageType, SendResult
+from gateway.run import GatewayRunner
+from gateway.session import SessionSource, build_session_key
+
+
+class RecordingAdapter(BasePlatformAdapter):
+    def __init__(self):
+        super().__init__(PlatformConfig(enabled=True, token="***"), Platform.TELEGRAM)
+        self.sent: list[str] = []
+
+    async def connect(self):
+        return True
+
+    async def disconnect(self):
+        return None
+
+    async def send(self, chat_id, content, reply_to=None, metadata=None):
+        self.sent.append(content)
+        return SendResult(success=True, message_id="1")
+
+    async def send_typing(self, chat_id, metadata=None):
+        return None
+
+    async def get_chat_info(self, chat_id):
+        return {"id": chat_id}
+
+
+def _source(chat_id="123456"):
+    return SessionSource(
+        platform=Platform.TELEGRAM,
+        chat_id=chat_id,
+        chat_type="dm",
+    )
+
+
+def _make_runner() -> tuple[GatewayRunner, RecordingAdapter]:
+    runner = object.__new__(GatewayRunner)
+    runner.config = GatewayConfig(platforms={Platform.TELEGRAM: PlatformConfig(enabled=True, token="***")})
+    runner.adapters = {}
+    runner._running = True
+    runner._shutdown_event = asyncio.Event()
+    runner._exit_reason = None
+    runner._exit_code = None
+    runner._running_agents = {}
+    runner._running_agents_ts = {}
+    runner._pending_messages = {}
+    runner._pending_approvals = {}
+    runner._background_tasks = set()
+    runner._draining = False
+    runner._restart_requested = False
+    runner._restart_task_started = False
+    runner._restart_detached = False
+    runner._restart_via_service = False
+    runner._restart_drain_timeout = 60.0
+    runner._stop_task = None
+    runner._busy_input_mode = "interrupt"
+    runner._update_prompt_pending = {}
+    runner._voice_mode = {}
+    runner._update_runtime_status = MagicMock()
+    runner._queue_or_replace_pending_event = GatewayRunner._queue_or_replace_pending_event.__get__(runner, GatewayRunner)
+    runner._session_key_for_source = GatewayRunner._session_key_for_source.__get__(runner, GatewayRunner)
+    runner._handle_active_session_busy_message = GatewayRunner._handle_active_session_busy_message.__get__(runner, GatewayRunner)
+    runner._handle_restart_command = GatewayRunner._handle_restart_command.__get__(runner, GatewayRunner)
+    runner._status_action_label = GatewayRunner._status_action_label.__get__(runner, GatewayRunner)
+    runner._status_action_gerund = GatewayRunner._status_action_gerund.__get__(runner, GatewayRunner)
+    runner._queue_during_drain_enabled = GatewayRunner._queue_during_drain_enabled.__get__(runner, GatewayRunner)
+    runner._running_agent_count = GatewayRunner._running_agent_count.__get__(runner, GatewayRunner)
+    runner.request_restart = MagicMock(return_value=True)
+    runner._is_user_authorized = lambda _source: True
+    runner.hooks = MagicMock()
+    runner.hooks.emit = AsyncMock()
+    runner.pairing_store = MagicMock()
+    runner.session_store = MagicMock()
+    runner.delivery_router = MagicMock()
+
+    adapter = RecordingAdapter()
+    adapter.set_message_handler(AsyncMock(return_value=None))
+    adapter.set_busy_session_handler(runner._handle_active_session_busy_message)
+    runner.adapters = {Platform.TELEGRAM: adapter}
+    return runner, adapter
+
+
+@pytest.mark.asyncio
+async def test_restart_command_while_busy_requests_drain_without_interrupt():
+    runner, _adapter = _make_runner()
+    event = MessageEvent(text="/restart", message_type=MessageType.TEXT, source=_source(), message_id="m1")
+    session_key = build_session_key(event.source)
+    running_agent = MagicMock()
+    runner._running_agents[session_key] = running_agent
+
+    result = await runner._handle_message(event)
+
+    assert result == "⏳ Draining 1 active agent(s) before restart..."
+    running_agent.interrupt.assert_not_called()
+    runner.request_restart.assert_called_once_with(detached=True, via_service=False)
+
+
+@pytest.mark.asyncio
+async def test_drain_queue_mode_queues_follow_up_without_interrupt():
+    runner, adapter = _make_runner()
+    runner._draining = True
+    runner._restart_requested = True
+    runner._busy_input_mode = "queue"
+
+    event = MessageEvent(text="follow up", message_type=MessageType.TEXT, source=_source(), message_id="m2")
+    session_key = build_session_key(event.source)
+    adapter._active_sessions[session_key] = asyncio.Event()
+
+    await adapter.handle_message(event)
+
+    assert session_key in adapter._pending_messages
+    assert adapter._pending_messages[session_key].text == "follow up"
+    assert not adapter._active_sessions[session_key].is_set()
+    assert any("queued for the next turn" in message for message in adapter.sent)
+
+
+@pytest.mark.asyncio
+async def test_draining_rejects_new_session_messages():
+    runner, _adapter = _make_runner()
+    runner._draining = True
+    runner._restart_requested = True
+
+    event = MessageEvent(text="hello", message_type=MessageType.TEXT, source=_source("fresh"), message_id="m3")
+
+    result = await runner._handle_message(event)
+
+    assert result == "⏳ Gateway is restarting and is not accepting new work right now."
diff --git a/tests/gateway/test_session_boundary_hooks.py b/tests/gateway/test_session_boundary_hooks.py
index 31e02980a7..a556624363 100644
--- a/tests/gateway/test_session_boundary_hooks.py
+++ b/tests/gateway/test_session_boundary_hooks.py
@@ -127,6 +127,16 @@ async def test_shutdown_fires_finalize_for_active_agents(mock_invoke_hook):
     runner._shutdown_event = MagicMock()
     runner.adapters = {}
     runner._exit_reason = "test"
+    runner._exit_code = None
+    runner._draining = False
+    runner._restart_requested = False
+    runner._restart_task_started = False
+    runner._restart_detached = False
+    runner._restart_via_service = False
+    runner._restart_drain_timeout = 0.0
+    runner._stop_task = None
+    runner._running_agents_ts = {}
+    runner._update_runtime_status = MagicMock()
 
     agent1 = MagicMock()
     agent1.session_id = "sess-a"
diff --git a/tests/gateway/test_session_race_guard.py b/tests/gateway/test_session_race_guard.py
index ff21cdef8c..7a4f6f1011 100644
--- a/tests/gateway/test_session_race_guard.py
+++ b/tests/gateway/test_session_race_guard.py
@@ -41,6 +41,15 @@ def _make_runner():
     runner._pending_approvals = {}
     runner._voice_mode = {}
     runner._background_tasks = set()
+    runner._draining = False
+    runner._restart_requested = False
+    runner._restart_task_started = False
+    runner._restart_detached = False
+    runner._restart_via_service = False
+    runner._restart_drain_timeout = 0.0
+    runner._stop_task = None
+    runner._exit_code = None
+    runner._update_runtime_status = MagicMock()
     runner._is_user_authorized = lambda _source: True
     runner.hooks = MagicMock()
     runner.hooks.emit = AsyncMock()
diff --git a/tests/hermes_cli/test_gateway_service.py b/tests/hermes_cli/test_gateway_service.py
index b32c7fe787..3586564e8e 100644
--- a/tests/hermes_cli/test_gateway_service.py
+++ b/tests/hermes_cli/test_gateway_service.py
@@ -74,7 +74,7 @@ class TestSystemdServiceRefresh:
         assert unit_path.read_text(encoding="utf-8") == "new unit\n"
         assert calls[:2] == [
             ["systemctl", "--user", "daemon-reload"],
-            ["systemctl", "--user", "restart", gateway_cli.get_service_name()],
+            ["systemctl", "--user", "reload-or-restart", gateway_cli.get_service_name()],
         ]
 
 
@@ -84,6 +84,8 @@ class TestGeneratedSystemdUnits:
 
         assert "ExecStart=" in unit
         assert "ExecStop=" not in unit
+        assert "ExecReload=/bin/kill -USR1 $MAINPID" in unit
+        assert "RestartForceExitStatus=75" in unit
         assert "TimeoutStopSec=60" in unit
 
     def test_user_unit_includes_resolved_node_directory_in_path(self, monkeypatch):
@@ -98,6 +100,8 @@ class TestGeneratedSystemdUnits:
 
         assert "ExecStart=" in unit
         assert "ExecStop=" not in unit
+        assert "ExecReload=/bin/kill -USR1 $MAINPID" in unit
+        assert "RestartForceExitStatus=75" in unit
         assert "TimeoutStopSec=60" in unit
         assert "WantedBy=multi-user.target" in unit
 
@@ -234,6 +238,31 @@ class TestLaunchdServiceRecovery:
             ["launchctl", "kickstart", target],
         ]
 
+    def test_launchd_restart_drains_running_gateway_before_kickstart(self, monkeypatch):
+        calls = []
+        target = f"{gateway_cli._launchd_domain()}/{gateway_cli.get_launchd_label()}"
+
+        monkeypatch.setattr(gateway_cli, "_get_restart_drain_timeout", lambda: 12.0)
+        monkeypatch.setattr(gateway_cli, "_wait_for_gateway_exit", lambda timeout, force_after=None: True)
+        monkeypatch.setattr(gateway_cli, "terminate_pid", lambda pid, force=False: calls.append(("term", pid, force)))
+        monkeypatch.setattr(
+            "gateway.status.get_running_pid",
+            lambda: 321,
+        )
+
+        def fake_run(cmd, check=False, **kwargs):
+            calls.append(cmd)
+            return SimpleNamespace(returncode=0, stdout="", stderr="")
+
+        monkeypatch.setattr(gateway_cli.subprocess, "run", fake_run)
+
+        gateway_cli.launchd_restart()
+
+        assert calls == [
+            ("term", 321, False),
+            ["launchctl", "kickstart", "-k", target],
+        ]
+
     def test_launchd_stop_uses_bootout_not_kill(self, monkeypatch):
         """launchd_stop must bootout the service so KeepAlive doesn't respawn it."""
         label = gateway_cli.get_launchd_label()