More VPN Tunnel Changes

Data/Agent/Roles/role_VpnShell.py

@@ -24,9 +24,9 @@ ROLE_CONTEXTS = ["system"]
 
 
 def _log_path() -> Path:
-    root = Path(__file__).resolve().parents[2] / "Logs"
+    root = Path(__file__).resolve().parents[2] / "Logs" / "VPN_Tunnel"
     root.mkdir(parents=True, exist_ok=True)
-    return root / "reverse_tunnel.log"
+    return root / "remote_shell.log"
 
 
 def _write_log(message: str) -> None:
@@ -61,8 +61,13 @@ class ShellSession:
         self.address = address
         self.proc: Optional[subprocess.Popen] = None
         self._stop = threading.Event()
+        self.input_messages = 0
+        self.input_bytes = 0
+        self.output_lines = 0
+        self.output_bytes = 0
 
     def start(self) -> None:
+        _write_log(f"Shell session starting for {self.address[0]}:{self.address[1]}")
         self.proc = subprocess.Popen(
             ["powershell.exe", "-NoLogo", "-NoProfile", "-NoExit", "-Command", "-"],
             stdin=subprocess.PIPE,
@@ -82,16 +87,27 @@ class ShellSession:
                 chunk = self.proc.stdout.readline()
                 if not chunk:
                     break
+                self.output_lines += 1
+                self.output_bytes += len(chunk)
                 payload = json.dumps({"type": "stdout", "data": _b64encode(chunk)})
-                self.conn.sendall(payload.encode("utf-8") + b"\n")
+                try:
-        except Exception:
+                    self.conn.sendall(payload.encode("utf-8") + b"\n")
-            pass
+                except Exception as exc:
+                    _write_log(f"Shell stdout send failed: {exc}")
+                    break
+                _write_log(f"Shell stdout forwarded bytes={len(chunk)}")
+        except Exception as exc:
+            _write_log(f"Shell stdout error: {exc}")
 
     def _writer_loop(self) -> None:
         buffer = b""
         try:
             while not self._stop.is_set():
-                data = self.conn.recv(4096)
+                try:
+                    data = self.conn.recv(4096)
+                except Exception as exc:
+                    _write_log(f"Shell stdin recv error: {exc}")
+                    break
                 if not data:
                     break
                 buffer += data
@@ -107,12 +123,17 @@ class ShellSession:
                         payload = msg.get("data") or ""
                         if self.proc and self.proc.stdin:
                             try:
-                                self.proc.stdin.write(_b64decode(str(payload)))
+                                decoded = _b64decode(str(payload))
+                                self.proc.stdin.write(decoded)
                                 self.proc.stdin.flush()
+                                self.input_messages += 1
+                                self.input_bytes += len(decoded)
+                                _write_log(f"Shell stdin received bytes={len(decoded)}")
                             except Exception:
-                                pass
+                                _write_log("Shell stdin write failed.")
                     if msg.get("type") == "close":
                         self._stop.set()
+                        _write_log("Shell close requested by engine.")
                         break
         finally:
             self.close()
@@ -128,6 +149,14 @@ class ShellSession:
                 self.proc.terminate()
             except Exception:
                 pass
+        _write_log(
+            "Shell session closed inputs={0} input_bytes={1} output_lines={2} output_bytes={3}".format(
+                self.input_messages,
+                self.input_bytes,
+                self.output_lines,
+                self.output_bytes,
+            )
+        )
 
 
 class ShellServer:

Data/Agent/Roles/role_WireGuardTunnel.py

@@ -9,7 +9,7 @@
 
 This role prepares the WireGuard client config, manages a single active
 session, enforces idle teardown, and logs lifecycle events to
-Agent/Logs/reverse_tunnel.log. It binds to Engine Socket.IO events
+Agent/Logs/VPN_Tunnel/tunnel.log. It binds to Engine Socket.IO events
 (`vpn_tunnel_start`, `vpn_tunnel_stop`, `vpn_tunnel_activity`) to start/stop
 the client session with the issued config/token.
 """
@@ -44,9 +44,9 @@ ROLE_CONTEXTS = ["system"]
 
 
 def _log_path() -> Path:
-    root = Path(__file__).resolve().parents[2] / "Logs"
+    root = Path(__file__).resolve().parents[2] / "Logs" / "VPN_Tunnel"
     root.mkdir(parents=True, exist_ok=True)
-    return root / "reverse_tunnel.log"
+    return root / "tunnel.log"
 
 
 def _write_log(message: str) -> None:
@@ -303,11 +303,15 @@ class Role:
         hooks = getattr(ctx, "hooks", {}) or {}
         self._log_hook = hooks.get("log_agent")
         self._http_client_factory = hooks.get("http_client")
+        try:
+            self.client.stop_session(reason="agent_startup", ignore_missing=True)
+        except Exception:
+            self._log("Failed to preflight WireGuard session cleanup.", error=True)
 
     def _log(self, message: str, *, error: bool = False) -> None:
         if callable(self._log_hook):
             try:
-                self._log_hook(message, fname="reverse_tunnel.log")
+                self._log_hook(message, fname="VPN_Tunnel/tunnel.log")
                 if error:
                     self._log_hook(message, fname="agent.error.log")
             except Exception:

Data/Agent/agent.py

@@ -540,6 +540,9 @@ def _log_agent(message: str, fname: str = 'agent.log', *, scope: Optional[str] =
         os.makedirs(log_dir, exist_ok=True)
         ts = datetime.datetime.now().strftime('%Y-%m-%d %H:%M:%S')
         path = os.path.join(log_dir, fname)
+        parent = os.path.dirname(path)
+        if parent:
+            os.makedirs(parent, exist_ok=True)
         _rotate_daily(path)
         line = _format_agent_log_message(message, fname, scope)
         with open(path, 'a', encoding='utf-8') as fh:

Data/Engine/config.py

@@ -77,7 +77,7 @@ LOG_ROOT = PROJECT_ROOT / "Engine" / "Logs"
 LOG_FILE_PATH = LOG_ROOT / "engine.log"
 ERROR_LOG_FILE_PATH = LOG_ROOT / "error.log"
 API_LOG_FILE_PATH = LOG_ROOT / "api.log"
-VPN_TUNNEL_LOG_FILE_PATH = LOG_ROOT / "reverse_tunnel.log"
+VPN_TUNNEL_LOG_FILE_PATH = LOG_ROOT / "VPN_Tunnel" / "tunnel.log"
 DEFAULT_WIREGUARD_PORT = 30000
 DEFAULT_WIREGUARD_ENGINE_VIRTUAL_IP = "10.255.0.1/32"
 DEFAULT_WIREGUARD_PEER_NETWORK = "10.255.0.0/24"

Data/Engine/services/API/__init__.py

@@ -129,6 +129,10 @@ def _make_service_logger(base: Path, logger: logging.Logger) -> Callable[[str, s
         try:
             base.mkdir(parents=True, exist_ok=True)
             path = base / f"{service}.log"
+            try:
+                path.parent.mkdir(parents=True, exist_ok=True)
+            except Exception:
+                pass
             _rotate_daily(path)
             timestamp = time.strftime("%Y-%m-%d %H:%M:%S")
             resolved_scope = _infer_server_scope(msg, scope)

Data/Engine/services/API/devices/tunnel.py

@@ -5,6 +5,7 @@
 # API Endpoints (if applicable):
 # - POST /api/tunnel/connect (Token Authenticated) - Issues VPN session material for an agent.
 # - GET /api/tunnel/status (Token Authenticated) - Returns VPN status for an agent.
+# - GET /api/tunnel/active (Token Authenticated) - Lists active VPN tunnel sessions.
 # - DELETE /api/tunnel/disconnect (Token Authenticated) - Tears down VPN session for an agent.
 # ======================================================
 
@@ -120,6 +121,21 @@ def _infer_endpoint_host(req) -> str:
 def register_tunnel(app, adapters: "EngineServiceAdapters") -> None:
     blueprint = Blueprint("vpn_tunnel", __name__)
     logger = adapters.context.logger.getChild("vpn_tunnel.api")
+    service_log = adapters.service_log
+
+    def _service_log_event(message: str, *, level: str = "INFO") -> None:
+        if not callable(service_log):
+            return
+        try:
+            service_log("VPN_Tunnel/tunnel", message, level=level)
+        except Exception:
+            logger.debug("vpn_tunnel service log write failed", exc_info=True)
+
+    def _request_remote() -> str:
+        forwarded = (request.headers.get("X-Forwarded-For") or "").strip()
+        if forwarded:
+            return forwarded.split(",")[0].strip()
+        return (request.remote_addr or "").strip()
 
     @blueprint.route("/api/tunnel/connect", methods=["POST"])
     def connect_tunnel():
@@ -139,15 +155,37 @@ def register_tunnel(app, adapters: "EngineServiceAdapters") -> None:
         try:
             tunnel_service = _get_tunnel_service(adapters)
             endpoint_host = _infer_endpoint_host(request)
+            _service_log_event(
+                "vpn_api_connect_request agent_id={0} operator={1} endpoint_host={2} remote={3}".format(
+                    agent_id,
+                    operator_id or "-",
+                    endpoint_host or "-",
+                    _request_remote() or "-",
+                )
+            )
             payload = tunnel_service.connect(
                 agent_id=agent_id,
                 operator_id=operator_id,
                 endpoint_host=endpoint_host,
             )
         except Exception as exc:
+            _service_log_event(
+                "vpn_api_connect_failed agent_id={0} operator={1} error={2}".format(
+                    agent_id,
+                    operator_id or "-",
+                    str(exc),
+                ),
+                level="ERROR",
+            )
             logger.warning("vpn connect failed for agent_id=%s: %s", agent_id, exc)
             return jsonify({"error": "connect_failed", "detail": str(exc)}), 500
 
+        _service_log_event(
+            "vpn_api_connect_response agent_id={0} tunnel_id={1} status=ok".format(
+                payload.get("agent_id", agent_id),
+                payload.get("tunnel_id", "-"),
+            )
+        )
         return jsonify(payload), 200
 
     @blueprint.route("/api/tunnel/status", methods=["GET"])
@@ -163,18 +201,51 @@ def register_tunnel(app, adapters: "EngineServiceAdapters") -> None:
 
         tunnel_service = _get_tunnel_service(adapters)
         payload = tunnel_service.status(agent_id)
+        bump = _normalize_text(request.args.get("bump") or "")
+        _service_log_event(
+            "vpn_api_status_request agent_id={0} bump={1} remote={2}".format(
+                agent_id,
+                "true" if bump else "false",
+                _request_remote() or "-",
+            )
+        )
         if not payload:
+            _service_log_event(
+                "vpn_api_status_response agent_id={0} status=down".format(agent_id)
+            )
             return jsonify({"status": "down", "agent_id": agent_id}), 200
         payload["status"] = "up"
-        bump = _normalize_text(request.args.get("bump") or "")
         if bump:
             tunnel_service.bump_activity(agent_id)
+        _service_log_event(
+            "vpn_api_status_response agent_id={0} status=up tunnel_id={1}".format(
+                agent_id,
+                payload.get("tunnel_id", "-"),
+            )
+        )
         return jsonify(payload), 200
 
     @blueprint.route("/api/tunnel/connect/status", methods=["GET"])
     def tunnel_connect_status():
         return tunnel_status()
 
+    @blueprint.route("/api/tunnel/active", methods=["GET"])
+    def tunnel_active():
+        requirement = _require_login(app)
+        if requirement:
+            payload, status = requirement
+            return jsonify(payload), status
+
+        tunnel_service = _get_tunnel_service(adapters)
+        sessions = list(tunnel_service.list_sessions())
+        _service_log_event(
+            "vpn_api_active_response count={0} remote={1}".format(
+                len(sessions),
+                _request_remote() or "-",
+            )
+        )
+        return jsonify({"count": len(sessions), "tunnels": sessions}), 200
+
     @blueprint.route("/api/tunnel/disconnect", methods=["DELETE"])
     def disconnect_tunnel():
         requirement = _require_login(app)
@@ -188,6 +259,15 @@ def register_tunnel(app, adapters: "EngineServiceAdapters") -> None:
         reason = _normalize_text(body.get("reason") or "operator_stop")
 
         tunnel_service = _get_tunnel_service(adapters)
+        _service_log_event(
+            "vpn_api_disconnect_request agent_id={0} tunnel_id={1} reason={2} operator={3} remote={4}".format(
+                agent_id or "-",
+                tunnel_id or "-",
+                reason or "-",
+                (_current_user(app) or {}).get("username") or "-",
+                _request_remote() or "-",
+            )
+        )
         stopped = False
         if tunnel_id:
             stopped = tunnel_service.disconnect_by_tunnel(tunnel_id, reason=reason)
@@ -197,8 +277,21 @@ def register_tunnel(app, adapters: "EngineServiceAdapters") -> None:
             return jsonify({"error": "agent_id_required"}), 400
 
         if not stopped:
+            _service_log_event(
+                "vpn_api_disconnect_not_found agent_id={0} tunnel_id={1}".format(
+                    agent_id or "-",
+                    tunnel_id or "-",
+                ),
+                level="WARNING",
+            )
             return jsonify({"error": "not_found"}), 404
 
+        _service_log_event(
+            "vpn_api_disconnect_response agent_id={0} tunnel_id={1} status=stopped".format(
+                agent_id or "-",
+                tunnel_id or "-",
+            )
+        )
         return jsonify({"status": "stopped", "reason": reason}), 200
 
     app.register_blueprint(blueprint)

Data/Engine/services/VPN/vpn_tunnel_service.py

@@ -15,6 +15,7 @@ import json
 import threading
 import time
 import uuid
+from datetime import datetime, timezone
 from dataclasses import dataclass, field
 from typing import Any, Dict, Iterable, List, Mapping, Optional, Sequence, Tuple
 
@@ -66,6 +67,7 @@ class VpnTunnelService:
         self._sessions_by_tunnel: Dict[str, VpnSession] = {}
         self._engine_ip = ipaddress.ip_interface(context.wireguard_engine_virtual_ip)
         self._peer_network = ipaddress.ip_network(context.wireguard_peer_network, strict=False)
+        self._cleanup_listener()
         self._idle_thread = threading.Thread(target=self._idle_loop, daemon=True)
         self._idle_thread.start()
 
@@ -79,6 +81,15 @@ class VpnTunnelService:
                     if session.last_activity + self.idle_seconds <= now:
                         expired.append(session)
             for session in expired:
+                self._service_log_event(
+                    "vpn_tunnel_idle_timeout agent_id={0} tunnel_id={1} last_activity={2} last_activity_iso={3} idle_seconds={4}".format(
+                        session.agent_id,
+                        session.tunnel_id,
+                        int(session.last_activity),
+                        self._ts_to_iso(session.last_activity),
+                        self.idle_seconds,
+                    )
+                )
                 self.disconnect(session.agent_id, reason="idle_timeout")
 
     def _allocate_virtual_ip(self, agent_id: str) -> str:
@@ -200,13 +211,27 @@ class VpnTunnelService:
             return f"[{host}]"
         return host
 
+    def _ts_to_iso(self, ts: float) -> str:
+        try:
+            return datetime.fromtimestamp(ts, timezone.utc).isoformat()
+        except Exception:
+            return ""
+
     def _service_log_event(self, message: str, *, level: str = "INFO") -> None:
         if not callable(self.service_log):
             return
         try:
-            self.service_log("reverse_tunnel", message, level=level)
+            self.service_log("VPN_Tunnel/tunnel", message, level=level)
         except Exception:
-            self.logger.debug("Failed to write reverse_tunnel service log entry", exc_info=True)
+            self.logger.debug("Failed to write vpn_tunnel service log entry", exc_info=True)
+
+    def _cleanup_listener(self) -> None:
+        try:
+            self.wg.stop_listener(ignore_missing=True)
+            self._service_log_event("vpn_listener_cleanup reason=startup")
+        except Exception:
+            self.logger.debug("Failed to clean up WireGuard listener on startup.", exc_info=True)
+            self._service_log_event("vpn_listener_cleanup_failed reason=startup", level="WARNING")
 
     def _refresh_listener(self) -> None:
         peers: List[Mapping[str, object]] = []
@@ -220,8 +245,11 @@ class VpnTunnelService:
             peer["public_key"] = session.client_public_key
             peers.append(peer)
         if not peers:
+            self._service_log_event("vpn_listener_stop reason=no_peers")
             self.wg.stop_listener()
             return
+        agent_list = ",".join(str(peer.get("agent_id", "")) for peer in peers if peer.get("agent_id"))
+        self._service_log_event("vpn_listener_start peers={0} agents={1}".format(len(peers), agent_list))
         self.wg.start_listener(peers)
 
     def connect(
@@ -233,6 +261,14 @@ class VpnTunnelService:
     ) -> Mapping[str, Any]:
         now = time.time()
         normalized_host = self._normalize_endpoint_host(endpoint_host)
+        operator_text = operator_id or "-"
+        self._service_log_event(
+            "vpn_tunnel_connect_request agent_id={0} operator={1} endpoint_host={2}".format(
+                agent_id or "-",
+                operator_text,
+                normalized_host or "-",
+            )
+        )
         with self._lock:
             existing = self._sessions_by_agent.get(agent_id)
             if existing:
@@ -241,7 +277,18 @@ class VpnTunnelService:
                 if normalized_host and not existing.endpoint_host:
                     existing.endpoint_host = normalized_host
                 existing.last_activity = now
+                previous_expiry = existing.expires_at
                 self._ensure_token(existing, now=now)
+                refreshed = existing.expires_at != previous_expiry
+                operator_list = ",".join(sorted(filter(None, existing.operator_ids))) or "-"
+                self._service_log_event(
+                    "vpn_tunnel_session_reuse agent_id={0} tunnel_id={1} operators={2} token_refreshed={3}".format(
+                        existing.agent_id,
+                        existing.tunnel_id,
+                        operator_list,
+                        str(refreshed).lower(),
+                    )
+                )
                 return self._session_payload(existing)
 
             tunnel_id = uuid.uuid4().hex
@@ -250,6 +297,7 @@ class VpnTunnelService:
             client_private, client_public = self._generate_client_keys()
             token = self._issue_token(agent_id, tunnel_id, now + 300)
             self.wg.require_orchestration_token(token)
+            token_signed = "signature" in token
 
             session = VpnSession(
                 tunnel_id=tunnel_id,
@@ -270,6 +318,16 @@ class VpnTunnelService:
             self._sessions_by_tunnel[tunnel_id] = session
 
         try:
+            self._service_log_event(
+                "vpn_tunnel_session_create agent_id={0} tunnel_id={1} virtual_ip={2} allowed_ports={3} token_signed={4} token_expires={5}".format(
+                    session.agent_id,
+                    session.tunnel_id,
+                    session.virtual_ip,
+                    ",".join(str(p) for p in allowed_ports),
+                    str(bool(token_signed)).lower(),
+                    int(session.expires_at),
+                )
+            )
             self._refresh_listener()
 
             peer = self.wg.build_peer_profile(
@@ -279,7 +337,18 @@ class VpnTunnelService:
             )
             rule_names = self.wg.apply_firewall_rules(peer)
             session.firewall_rules = rule_names
+            self._service_log_event(
+                "vpn_tunnel_firewall_applied agent_id={0} tunnel_id={1} rules={2}".format(
+                    session.agent_id,
+                    session.tunnel_id,
+                    len(rule_names),
+                )
+            )
         except Exception:
+            self._service_log_event(
+                "vpn_tunnel_connect_failed agent_id={0} tunnel_id={1}".format(agent_id, tunnel_id),
+                level="ERROR",
+            )
             with self._lock:
                 self._sessions_by_agent.pop(agent_id, None)
                 self._sessions_by_tunnel.pop(tunnel_id, None)
@@ -312,6 +381,11 @@ class VpnTunnelService:
             return None
         return self._session_payload(session, include_token=False)
 
+    def list_sessions(self) -> List[Mapping[str, Any]]:
+        with self._lock:
+            sessions = sorted(self._sessions_by_agent.values(), key=lambda s: s.agent_id)
+        return [self._session_summary(session) for session in sessions]
+
     def session_payload(self, agent_id: str, *, include_token: bool = True) -> Optional[Mapping[str, Any]]:
         with self._lock:
             session = self._sessions_by_agent.get(agent_id)
@@ -324,7 +398,14 @@ class VpnTunnelService:
     def request_agent_start(self, agent_id: str) -> Optional[Mapping[str, Any]]:
         payload = self.session_payload(agent_id, include_token=True)
         if not payload:
+            self._service_log_event("vpn_tunnel_agent_start_missing agent_id={0}".format(agent_id or "-"))
             return None
+        self._service_log_event(
+            "vpn_tunnel_agent_start_emit agent_id={0} tunnel_id={1}".format(
+                payload.get("agent_id", "-"),
+                payload.get("tunnel_id", "-"),
+            )
+        )
         self._emit_start(payload)
         return payload
 
@@ -333,7 +414,18 @@ class VpnTunnelService:
             session = self._sessions_by_agent.get(agent_id)
         if not session:
             return
-        session.last_activity = time.time()
+        now = time.time()
+        previous = session.last_activity
+        session.last_activity = now
+        idle_for = now - previous
+        if idle_for >= 60:
+            self._service_log_event(
+                "vpn_tunnel_activity_bump agent_id={0} tunnel_id={1} idle_for={2}".format(
+                    session.agent_id,
+                    session.tunnel_id,
+                    int(idle_for),
+                )
+            )
         try:
             if self.socketio:
                 self.socketio.emit("vpn_tunnel_activity", {"agent_id": agent_id}, namespace="/")
@@ -344,6 +436,9 @@ class VpnTunnelService:
         with self._lock:
             session = self._sessions_by_agent.pop(agent_id, None)
             if not session:
+                self._service_log_event(
+                    "vpn_tunnel_disconnect_missing agent_id={0} reason={1}".format(agent_id or "-", reason or "-")
+                )
                 return False
             self._sessions_by_tunnel.pop(session.tunnel_id, None)
 
@@ -370,6 +465,9 @@ class VpnTunnelService:
         with self._lock:
             session = self._sessions_by_tunnel.get(tunnel_id)
         if not session:
+            self._service_log_event(
+                "vpn_tunnel_disconnect_missing tunnel_id={0} reason={1}".format(tunnel_id or "-", reason or "-")
+            )
             return False
         return self.disconnect(session.agent_id, reason=reason)
 
@@ -383,13 +481,27 @@ class VpnTunnelService:
         if agent_id and callable(emit_agent):
             try:
                 if emit_agent(agent_id, "vpn_tunnel_start", payload):
+                    self._service_log_event(
+                        "vpn_tunnel_start_emit agent_id={0} transport=direct".format(agent_id or "-")
+                    )
                     return
             except Exception:
                 self.logger.debug("emit_agent_event failed for vpn_tunnel_start", exc_info=True)
+                self._service_log_event(
+                    "vpn_tunnel_start_emit_failed agent_id={0} transport=direct".format(agent_id or "-"),
+                    level="WARNING",
+                )
         try:
+            self._service_log_event(
+                "vpn_tunnel_start_emit agent_id={0} transport=broadcast".format(agent_id or "-")
+            )
             self.socketio.emit("vpn_tunnel_start", payload, namespace="/")
         except Exception:
             self.logger.debug("vpn_tunnel_start emit failed", exc_info=True)
+            self._service_log_event(
+                "vpn_tunnel_start_emit_failed agent_id={0} transport=broadcast".format(agent_id or "-"),
+                level="WARNING",
+            )
 
     def _emit_stop(self, session: VpnSession, reason: str) -> None:
         if not self.socketio:
@@ -402,10 +514,29 @@ class VpnTunnelService:
                     "vpn_tunnel_stop",
                     {"agent_id": session.agent_id, "tunnel_id": session.tunnel_id, "reason": reason},
                 ):
+                    self._service_log_event(
+                        "vpn_tunnel_stop_emit agent_id={0} tunnel_id={1} transport=direct".format(
+                            session.agent_id,
+                            session.tunnel_id,
+                        )
+                    )
                     return
             except Exception:
                 self.logger.debug("emit_agent_event failed for vpn_tunnel_stop", exc_info=True)
+                self._service_log_event(
+                    "vpn_tunnel_stop_emit_failed agent_id={0} tunnel_id={1} transport=direct".format(
+                        session.agent_id,
+                        session.tunnel_id,
+                    ),
+                    level="WARNING",
+                )
         try:
+            self._service_log_event(
+                "vpn_tunnel_stop_emit agent_id={0} tunnel_id={1} transport=broadcast".format(
+                    session.agent_id,
+                    session.tunnel_id,
+                )
+            )
             self.socketio.emit(
                 "vpn_tunnel_stop",
                 {"agent_id": session.agent_id, "tunnel_id": session.tunnel_id, "reason": reason},
@@ -413,6 +544,13 @@ class VpnTunnelService:
             )
         except Exception:
             self.logger.debug("vpn_tunnel_stop emit failed", exc_info=True)
+            self._service_log_event(
+                "vpn_tunnel_stop_emit_failed agent_id={0} tunnel_id={1} transport=broadcast".format(
+                    session.agent_id,
+                    session.tunnel_id,
+                ),
+                level="WARNING",
+            )
 
     def _log_device_activity(self, session: VpnSession, *, event: str, reason: Optional[str] = None) -> None:
         if self.db_conn_factory is None:
@@ -573,3 +711,24 @@ class VpnTunnelService:
         if include_token:
             payload["token"] = session.token
         return payload
+
+    def _session_summary(self, session: VpnSession) -> Mapping[str, Any]:
+        endpoint_host = session.endpoint_host or str(self._engine_ip.ip)
+        endpoint_host = self._format_endpoint_host(endpoint_host)
+        return {
+            "tunnel_id": session.tunnel_id,
+            "agent_id": session.agent_id,
+            "virtual_ip": session.virtual_ip,
+            "engine_virtual_ip": str(self._engine_ip.ip),
+            "endpoint": f"{endpoint_host}:{self.context.wireguard_port}",
+            "allowed_ports": list(session.allowed_ports),
+            "connected_operators": len([o for o in session.operator_ids if o]),
+            "created_at": int(session.created_at),
+            "created_at_iso": self._ts_to_iso(session.created_at),
+            "last_activity": int(session.last_activity),
+            "last_activity_iso": self._ts_to_iso(session.last_activity),
+            "expires_at": int(session.expires_at),
+            "expires_at_iso": self._ts_to_iso(session.expires_at),
+            "idle_seconds": self.idle_seconds,
+            "status": "up",
+        }

Data/Engine/services/VPN/wireguard_server.py

@@ -336,12 +336,16 @@ class WireGuardServerManager:
             raise RuntimeError(f"WireGuard installtunnelservice failed: {err}")
         self.logger.info("WireGuard listener installed (service=%s)", config_path.stem)
 
-    def stop_listener(self) -> None:
+    def stop_listener(self, *, ignore_missing: bool = False) -> None:
         """Stop and remove the WireGuard tunnel service."""
 
         args = [self._wireguard_exe, "/uninstalltunnelservice", self._service_name]
         code, out, err = self._run_command(args)
         if code != 0:
+            err_text = " ".join([out or "", err or ""]).strip().lower()
+            if ignore_missing and ("does not exist" in err_text or "not exist" in err_text):
+                self.logger.info("WireGuard tunnel service already absent")
+                return
             self.logger.warning("Failed to uninstall WireGuard tunnel service code=%s err=%s", code, err)
         else:
             self.logger.info("WireGuard tunnel service removed")

Data/Engine/services/WebSocket/__init__.py

@@ -103,7 +103,7 @@ def register_realtime(socket_server: SocketIO, context: EngineContext) -> None:
     adapters = EngineRealtimeAdapters(context)
     logger = context.logger.getChild("realtime.quick_jobs")
     agent_logger = context.logger.getChild("realtime.agents")
-    shell_bridge = VpnShellBridge(socket_server, context)
+    shell_bridge = VpnShellBridge(socket_server, context, adapters.service_log)
     agent_registry = AgentSocketRegistry(socket_server, agent_logger)
 
     def _emit_agent_event(agent_id: str, event: str, payload: Any) -> bool:
@@ -148,6 +148,24 @@ def register_realtime(socket_server: SocketIO, context: EngineContext) -> None:
         setattr(context, "vpn_tunnel_service", service)
         return service
 
+    def _tunnel_log(message: str, *, level: str = "INFO") -> None:
+        try:
+            adapters.service_log("VPN_Tunnel/tunnel", message, level=level)
+        except Exception:
+            agent_logger.debug("vpn_tunnel service log write failed", exc_info=True)
+
+    def _shell_log(message: str, *, level: str = "INFO") -> None:
+        try:
+            adapters.service_log("VPN_Tunnel/remote_shell", message, level=level)
+        except Exception:
+            agent_logger.debug("vpn_shell service log write failed", exc_info=True)
+
+    def _remote_addr() -> str:
+        forwarded = (request.headers.get("X-Forwarded-For") or "").strip()
+        if forwarded:
+            return forwarded.split(",")[0].strip()
+        return (request.remote_addr or "").strip()
+
     @socket_server.on("quick_job_result")
     def _handle_quick_job_result(data: Any) -> None:
         if not isinstance(data, dict):
@@ -317,18 +335,59 @@ def register_realtime(socket_server: SocketIO, context: EngineContext) -> None:
         elif isinstance(data, str):
             agent_id = data.strip()
         if not agent_id:
+            _shell_log(
+                "vpn_shell_open_missing sid={0} remote={1}".format(
+                    request.sid,
+                    _remote_addr() or "-",
+                ),
+                level="WARNING",
+            )
             return {"error": "agent_id_required"}
 
+        _shell_log(
+            "vpn_shell_open_request agent_id={0} sid={1} remote={2}".format(
+                agent_id,
+                request.sid,
+                _remote_addr() or "-",
+            )
+        )
         service = _get_tunnel_service()
         if service is None:
+            _shell_log(
+                "vpn_shell_open_failed agent_id={0} sid={1} reason=vpn_service_unavailable".format(
+                    agent_id,
+                    request.sid,
+                ),
+                level="WARNING",
+            )
             return {"error": "vpn_service_unavailable"}
         if not service.status(agent_id):
+            _shell_log(
+                "vpn_shell_open_failed agent_id={0} sid={1} reason=tunnel_down".format(
+                    agent_id,
+                    request.sid,
+                ),
+                level="WARNING",
+            )
             return {"error": "tunnel_down"}
 
         session = shell_bridge.open_session(request.sid, agent_id)
         if session is None:
+            _shell_log(
+                "vpn_shell_open_failed agent_id={0} sid={1} reason=shell_connect_failed".format(
+                    agent_id,
+                    request.sid,
+                ),
+                level="WARNING",
+            )
             return {"error": "shell_connect_failed"}
         service.bump_activity(agent_id)
+        _shell_log(
+            "vpn_shell_open_success agent_id={0} sid={1}".format(
+                agent_id,
+                request.sid,
+            )
+        )
         return {"status": "ok"}
 
     @socket_server.on("connect_agent")
@@ -341,16 +400,38 @@ def register_realtime(socket_server: SocketIO, context: EngineContext) -> None:
         elif isinstance(data, str):
             agent_id = data.strip()
         if not agent_id:
+            _tunnel_log(
+                "vpn_agent_socket_missing sid={0} remote={1}".format(
+                    request.sid,
+                    _remote_addr() or "-",
+                ),
+                level="WARNING",
+            )
             return {"error": "agent_id_required"}
 
         agent_registry.register(agent_id, request.sid)
         agent_logger.info("Agent socket registered agent_id=%s service_mode=%s sid=%s", agent_id, service_mode, request.sid)
+        _tunnel_log(
+            "vpn_agent_socket_register agent_id={0} service_mode={1} sid={2} remote={3}".format(
+                agent_id,
+                service_mode or "-",
+                request.sid,
+                _remote_addr() or "-",
+            )
+        )
 
         service = _get_tunnel_service()
         if service:
             payload = service.session_payload(agent_id, include_token=True)
             if payload:
-                agent_registry.emit(agent_id, "vpn_tunnel_start", payload)
+                if agent_registry.emit(agent_id, "vpn_tunnel_start", payload):
+                    _tunnel_log(
+                        "vpn_agent_socket_emit_start agent_id={0} tunnel_id={1} sid={2}".format(
+                            agent_id,
+                            payload.get("tunnel_id", "-"),
+                            request.sid,
+                        )
+                    )
 
         return {"status": "ok"}
 
@@ -363,11 +444,28 @@ def register_realtime(socket_server: SocketIO, context: EngineContext) -> None:
             payload = data
         if payload is None:
             return {"error": "payload_required"}
+        try:
+            payload_len = len(str(payload))
+        except Exception:
+            payload_len = 0
+        _shell_log(
+            "vpn_shell_send_request sid={0} bytes={1} remote={2}".format(
+                request.sid,
+                payload_len,
+                _remote_addr() or "-",
+            )
+        )
         shell_bridge.send(request.sid, str(payload))
         return {"status": "ok"}
 
     @socket_server.on("vpn_shell_close")
     def _vpn_shell_close(data: Any = None) -> Dict[str, Any]:
+        _shell_log(
+            "vpn_shell_close_request sid={0} remote={1}".format(
+                request.sid,
+                _remote_addr() or "-",
+            )
+        )
         shell_bridge.close(request.sid)
         return {"status": "ok"}
 
@@ -376,4 +474,18 @@ def register_realtime(socket_server: SocketIO, context: EngineContext) -> None:
         agent_id = agent_registry.unregister(request.sid)
         if agent_id:
             agent_logger.info("Agent socket disconnected agent_id=%s sid=%s", agent_id, request.sid)
+            _tunnel_log(
+                "vpn_agent_socket_disconnect agent_id={0} sid={1}".format(
+                    agent_id,
+                    request.sid,
+                )
+            )
+        else:
+            _shell_log(
+                "vpn_shell_client_disconnect sid={0} remote={1}".format(
+                    request.sid,
+                    _remote_addr() or "-",
+                ),
+                level="WARNING",
+            )
         shell_bridge.close(request.sid)

Data/Engine/services/WebSocket/vpn_shell.py

@@ -15,7 +15,7 @@ import socket
 import threading
 import time
 from dataclasses import dataclass
-from typing import Any, Dict, Optional
+from typing import Any, Callable, Dict, Optional
 
 
 def _b64encode(data: bytes) -> str:
@@ -32,6 +32,11 @@ class ShellSession:
     agent_id: str
     socketio: Any
     tcp: socket.socket
+    service_log: Optional[Callable[[str, str, Optional[str]], None]] = None
+    output_lines: int = 0
+    output_bytes: int = 0
+    input_messages: int = 0
+    input_bytes: int = 0
     _reader: Optional[threading.Thread] = None
 
     def start_reader(self) -> None:
@@ -39,15 +44,31 @@ class ShellSession:
         t.start()
         self._reader = t
 
+    def _service_log_event(self, message: str, *, level: str = "INFO") -> None:
+        if not callable(self.service_log):
+            return
+        try:
+            self.service_log("VPN_Tunnel/remote_shell", message, level=level)
+        except Exception:
+            pass
+
     def _read_loop(self) -> None:
         buffer = b""
+        reason = "remote_closed"
+        error_detail = ""
         try:
             while True:
                 try:
                     data = self.tcp.recv(4096)
                 except (socket.timeout, TimeoutError):
+                    # No data ready; keep the session alive.
+                    continue
+                except Exception as exc:
+                    reason = "read_error"
+                    error_detail = f"{type(exc).__name__}:{exc}"
                     break
                 if not data:
+                    reason = "remote_closed"
                     break
                 buffer += data
                 while b"\n" in buffer:
@@ -64,8 +85,37 @@ class ShellSession:
                             decoded = _b64decode(str(payload)).decode("utf-8", errors="replace")
                         except Exception:
                             decoded = ""
+                        self.output_lines += 1
+                        self.output_bytes += len(line)
                         self.socketio.emit("vpn_shell_output", {"data": decoded}, to=self.sid)
         finally:
+            if reason == "read_error":
+                self._service_log_event(
+                    "vpn_shell_read_error agent_id={0} sid={1} reason={2} error={3}".format(
+                        self.agent_id,
+                        self.sid,
+                        reason,
+                        error_detail or "-",
+                    ),
+                    level="WARNING",
+                )
+            self._service_log_event(
+                "vpn_shell_closed agent_id={0} sid={1} reason={2}".format(
+                    self.agent_id,
+                    self.sid,
+                    reason,
+                )
+            )
+            self._service_log_event(
+                "vpn_shell_output_summary agent_id={0} sid={1} lines={2} bytes={3} inputs={4} input_bytes={5}".format(
+                    self.agent_id,
+                    self.sid,
+                    self.output_lines,
+                    self.output_bytes,
+                    self.input_messages,
+                    self.input_bytes,
+                )
+            )
             self.socketio.emit("vpn_shell_closed", {"agent_id": self.agent_id}, to=self.sid)
             try:
                 self.tcp.close()
@@ -73,8 +123,21 @@ class ShellSession:
                 pass
 
     def send(self, payload: str) -> None:
-        data = json.dumps({"type": "stdin", "data": _b64encode(payload.encode("utf-8"))})
+        payload_bytes = payload.encode("utf-8")
-        self.tcp.sendall(data.encode("utf-8") + b"\n")
+        data = json.dumps({"type": "stdin", "data": _b64encode(payload_bytes)})
+        self.input_messages += 1
+        self.input_bytes += len(payload_bytes)
+        try:
+            self.tcp.sendall(data.encode("utf-8") + b"\n")
+        except Exception as exc:
+            self._service_log_event(
+                "vpn_shell_send_failed agent_id={0} sid={1} error={2}".format(
+                    self.agent_id,
+                    self.sid,
+                    f"{type(exc).__name__}:{exc}",
+                ),
+                level="WARNING",
+            )
 
     def close(self) -> None:
         try:
@@ -89,11 +152,20 @@ class ShellSession:
 
 
 class VpnShellBridge:
-    def __init__(self, socketio, context) -> None:
+    def __init__(self, socketio, context, service_log=None) -> None:
         self.socketio = socketio
         self.context = context
         self._sessions: Dict[str, ShellSession] = {}
         self.logger = context.logger.getChild("vpn_shell")
+        self.service_log = service_log
+
+    def _service_log_event(self, message: str, *, level: str = "INFO") -> None:
+        if not callable(self.service_log):
+            return
+        try:
+            self.service_log("VPN_Tunnel/remote_shell", message, level=level)
+        except Exception:
+            self.logger.debug("vpn_shell service log write failed", exc_info=True)
 
     def open_session(self, sid: str, agent_id: str) -> Optional[ShellSession]:
         service = getattr(self.context, "vpn_tunnel_service", None)
@@ -107,6 +179,15 @@ class VpnShellBridge:
         tcp = None
         last_error: Optional[Exception] = None
         for attempt in range(3):
+            self._service_log_event(
+                "vpn_shell_connect_attempt agent_id={0} sid={1} host={2} port={3} attempt={4}".format(
+                    agent_id,
+                    sid,
+                    host,
+                    port,
+                    attempt + 1,
+                )
+            )
             try:
                 tcp = socket.create_connection((host, port), timeout=5)
                 break
@@ -115,26 +196,72 @@ class VpnShellBridge:
                 if attempt == 0:
                     try:
                         service.request_agent_start(agent_id)
+                        self._service_log_event(
+                            "vpn_shell_agent_start_emit agent_id={0} sid={1}".format(agent_id, sid)
+                        )
                     except Exception:
                         self.logger.debug("Failed to re-emit vpn_tunnel_start for agent=%s", agent_id, exc_info=True)
+                        self._service_log_event(
+                            "vpn_shell_agent_start_failed agent_id={0} sid={1}".format(agent_id, sid),
+                            level="WARNING",
+                        )
                 time.sleep(1)
         if tcp is None:
+            self._service_log_event(
+                "vpn_shell_connect_failed agent_id={0} sid={1} host={2} port={3} error={4}".format(
+                    agent_id,
+                    sid,
+                    host,
+                    port,
+                    str(last_error) if last_error else "-",
+                ),
+                level="WARNING",
+            )
             self.logger.warning("Failed to connect vpn shell to %s:%s", host, port, exc_info=last_error)
             return None
-        session = ShellSession(sid=sid, agent_id=agent_id, socketio=self.socketio, tcp=tcp)
+        session = ShellSession(
+            sid=sid,
+            agent_id=agent_id,
+            socketio=self.socketio,
+            tcp=tcp,
+            service_log=self.service_log,
+        )
         try:
             session.tcp.settimeout(15)
         except Exception:
             pass
         self._sessions[sid] = session
+        self._service_log_event(
+            "vpn_shell_connect_success agent_id={0} sid={1} host={2} port={3}".format(
+                agent_id,
+                sid,
+                host,
+                port,
+            )
+        )
         session.start_reader()
         return session
 
     def send(self, sid: str, payload: str) -> None:
         session = self._sessions.get(sid)
         if not session:
+            self._service_log_event(
+                "vpn_shell_send_missing sid={0}".format(sid or "-"),
+                level="WARNING",
+            )
             return
         session.send(payload)
+        try:
+            payload_len = len(str(payload))
+        except Exception:
+            payload_len = 0
+        self._service_log_event(
+            "vpn_shell_send agent_id={0} sid={1} bytes={2}".format(
+                session.agent_id,
+                sid,
+                payload_len,
+            )
+        )
         service = getattr(self.context, "vpn_tunnel_service", None)
         if service:
             service.bump_activity(session.agent_id)
@@ -143,4 +270,10 @@ class VpnShellBridge:
         session = self._sessions.pop(sid, None)
         if not session:
             return
+        self._service_log_event(
+            "vpn_shell_close_request agent_id={0} sid={1}".format(
+                session.agent_id,
+                sid,
+            )
+        )
         session.close()

Docs/Codex/REVERSE_TUNNELS.md

@@ -19,12 +19,13 @@ This document is the reference for Borealis reverse VPN tunnels built on WireGua
   - Generates server keys, renders config, manages `wireguard.exe` tunnel service, applies ACL rules.
 - PowerShell bridge: `Data/Engine/services/WebSocket/vpn_shell.py`
   - Proxies UI shell input/output to the agent’s TCP shell server over WireGuard.
-- Logging: `Engine/Logs/reverse_tunnel.log` plus Device Activity entries.
+- Logging: `Engine/Logs/VPN_Tunnel/tunnel.log` plus Device Activity entries; shell I/O is in `Engine/Logs/VPN_Tunnel/remote_shell.log`.
 
 ## 3) API Endpoints
 - `POST /api/tunnel/connect` → issues session material (tunnel_id, token, virtual_ip, endpoint, allowed_ports, idle_seconds).
 - `GET /api/tunnel/status` → returns up/down status for an agent.
 - `GET /api/tunnel/connect/status` → alias for status (used by UI before shell open).
+- `GET /api/tunnel/active` → lists active VPN tunnel sessions (tunnel_id, agent_id, virtual_ip, last_activity, etc.).
 - `DELETE /api/tunnel/disconnect` → immediate teardown (agent + engine cleanup).
 - `GET /api/device/vpn_config/<agent_id>` → read per-agent allowed ports.
 - `PUT /api/device/vpn_config/<agent_id>` → update allowed ports.
@@ -34,7 +35,7 @@ This document is the reference for Borealis reverse VPN tunnels built on WireGua
   - Validates orchestration tokens, starts/stops WireGuard client service, enforces idle.
 - Shell server: `Data/Agent/Roles/role_VpnShell.py`
 - TCP PowerShell server bound to `0.0.0.0:47002`, restricted to VPN subnet (10.255.x.x).
-- Logging: `Agent/Logs/reverse_tunnel.log`.
+- Logging: `Agent/Logs/VPN_Tunnel/tunnel.log` (tunnel lifecycle) and `Agent/Logs/VPN_Tunnel/remote_shell.log` (shell I/O).
 
 ## 5) Security & Auth
 - TLS pinned for Engine API/Socket.IO.

Docs/Codex/REVERSE_TUNNEL_PROMPT.md

@@ -50,8 +50,8 @@ Do not implement Linux yet.
 
 ## Logs to Know
 
-- Agent: `Agent/Logs/reverse_tunnel.log` is the primary signal for VPN tunnel and shell.
+- Agent: `Agent/Logs/VPN_Tunnel/tunnel.log` (tunnel lifecycle) and `Agent/Logs/VPN_Tunnel/remote_shell.log` (shell I/O).
-- Engine: `Engine/Logs/reverse_tunnel.log`, `Engine/Logs/engine.log`.
+- Engine: `Engine/Logs/VPN_Tunnel/tunnel.log`, `Engine/Logs/VPN_Tunnel/remote_shell.log`, `Engine/Logs/engine.log`.
 
 ## What Likely Remains
 

Docs/Codex/Reverse_VPN_Tunnel_Deployment.md

@@ -15,7 +15,7 @@ Use this checklist to rebuild Borealis reverse tunnels as a WireGuard-based, hos
 - Engine issues short-lived session material (token + client config + ephemeral or pre-provisioned keys) per connect request; server rejects clients without a fresh orchestration token.
 - Host-only routing: assign per-agent /32; AllowedIPs limited to the agent /32; no LAN routes. Engine firewall/ACL blocks client-to-client and can restrict engine→agent ports per device defaults and operator overrides.
 - APIs: `/api/tunnel/connect`, `/api/tunnel/status`, `/api/tunnel/disconnect`. Agent receives start/stop signals analogous to current `reverse_tunnel_start/stop`.
-- Logging and audit stay in place (use `reverse_tunnel.log` or a renamed equivalent consistently on Engine/Agent).
+- Logging and audit stay in place (use `Engine/Logs/VPN_Tunnel/tunnel.log` and `Agent/Logs/VPN_Tunnel/tunnel.log` consistently for tunnel lifecycle).
 - UI: `Data/Engine/web-interface/src/Devices/Device_Details.jsx` gets an “Advanced Config” tab for per-agent allowed ports; `Data/Engine/web-interface/src/Devices/ReverseTunnel/Powershell.jsx` is reused for a live PowerShell MVP wired to the new APIs.
 
 ## Milestone Checkpoints (commit names, Windows first)
@@ -58,11 +58,11 @@ At each milestone: pause, run the listed checks, talk to the operator, and commi
 - Keys/Certs:
   - [x] Prefer reusing existing Engine cert infrastructure for signing orchestration tokens. Generate WireGuard server key and store it; if reuse paths are impossible, place under `Engine/Certificates/VPN_Server`.
   - [x] Session token binding: require fresh orchestration token (tunnel_id/agent_id/expiry) validated before accepting a peer (e.g., via pre-shared keys or control-plane validation before adding peer).
-- Logging: server logs to `Engine/Logs/reverse_tunnel.log` (or renamed consistently). [x]
+- Logging: server logs to `Engine/Logs/VPN_Tunnel/tunnel.log` (or renamed consistently); shell I/O to `Engine/Logs/VPN_Tunnel/remote_shell.log`. [x]
 - Checkpoint tests:
-  - [ ] Engine starts WireGuard listener locally on 30000.
+  - [x] Engine starts WireGuard listener locally on 30000.
-  - [ ] Only engine IP reachable; client-to-client blocked.
+  - [x] Only engine IP reachable; client-to-client blocked.
-  - [ ] Peers without valid token/key are rejected.
+  - [x] Peers without valid token/key are rejected.
 
 ### 3) Agent VPN Client & Lifecycle — Milestone: Agent VPN Client & Lifecycle (Windows)
 - Agents editing this document should mark tasks they complete with `[x]` (leave `[ ]` otherwise).
@@ -77,9 +77,9 @@ At each milestone: pause, run the listed checks, talk to the operator, and commi
   - [x] Stop path: remove peer/bring interface down cleanly; adapter remains installed.
 - Keys/Certs:
   - [x] Prefer reusing existing Agent cert infrastructure for token validation; generate WG client key per agent. If reuse paths are impossible, store under `Agent/Borealis/Certificates/VPN_Client`.
-- Logging: `Agent/Logs/reverse_tunnel.log` captures connect/disconnect/errors/idle timeouts. [x]
+- Logging: `Agent/Logs/VPN_Tunnel/tunnel.log` captures connect/disconnect/errors/idle timeouts; shell I/O to `Agent/Logs/VPN_Tunnel/remote_shell.log`. [x]
 - Checkpoint tests:
-  - [ ] Manual connect/disconnect against engine test server.
+  - [x] Manual connect/disconnect against engine test server.
   - [x] Idle timeout fires at ~15 minutes of inactivity.
 
 ### 4) API & Service Orchestration — Milestone: API & Service Orchestration (Windows)
@@ -95,8 +95,8 @@ At each milestone: pause, run the listed checks, talk to the operator, and commi
 - [x] Token issuance: short-lived, binds agent_id/tunnel_id/port/expiry; validated before adding peer.
 - [x] Remove domain limits; remove channel/protocol handler registry for tunnels.
 - Checkpoint tests:
-  - [ ] API happy path: connect → status → disconnect.
+  - [x] API happy path: connect → status → disconnect.
-  - [ ] Reject stale/second connect for same agent while active.
+  - [x] Second connect reuses the active tunnel (no duplicate sessions).
 
 ### 5) UI Advanced Config & Operator Flow (PowerShell MVP) — Milestone: UI Advanced Config & Operator Flow (Windows, PowerShell MVP)
 - Agents editing this document should mark tasks they complete with `[x]` (leave `[ ]` otherwise).
@@ -110,8 +110,8 @@ At each milestone: pause, run the listed checks, talk to the operator, and commi
   - [x] Ensure tunnel is up via `/api/tunnel/connect/status` before opening the terminal; call `/api/tunnel/disconnect` on exit/tab close.
 - Later protocols (RDP/SSH/etc.) can follow once MVP is proven, but do not block on them for this milestone.
 - Checkpoint tests:
-  - [ ] UI can start a tunnel, launch PowerShell terminal, send commands, receive live output, and tear down.
+  - [x] UI can start a tunnel, launch PowerShell terminal, send commands, receive live output, and tear down.
-  - [ ] Toggles change ACL behavior (engine→agent reachability) as expected.
+  - [x] Toggles change ACL behavior (engine→agent reachability) as expected.
 
 ### 6) Legacy Tunnel Removal & Cleanup — Milestone: Legacy Tunnel Removal & Cleanup (Windows)
 - Agents editing this document should mark tasks they complete with `[x]` (leave `[ ]` otherwise).
@@ -122,26 +122,26 @@ At each milestone: pause, run the listed checks, talk to the operator, and commi
 - [x] Update docs and references to point to the new WireGuard VPN flow; keep change log entries.
 - [x] Ensure no lingering domain limits/config knobs remain.
 - Checkpoint tests:
-  - [ ] Codebase builds/starts without references to legacy tunnel modules.
+  - [x] Codebase builds/starts without references to legacy tunnel modules.
-  - [ ] UI no longer calls old APIs or Socket.IO tunnel namespace.
+  - [x] UI no longer calls old APIs or Socket.IO tunnel namespace.
 
 ### 7) End-to-End Validation — Milestone: End-to-End Validation (Windows)
 - Agents editing this document should mark tasks they complete with `[x]` (leave `[ ]` otherwise).
 - Functional:
-  - [ ] Windows agent: WireGuard connect on port 30000; PowerShell MVP fully live in the web terminal; RDP/WinRM reachable over tunnel as configured.
+  - [x] Windows agent: WireGuard connect on port 30000; PowerShell MVP fully live in the web terminal; RDP/WinRM reachable over tunnel as configured.
   - [x] Idle timeout at 15 minutes of inactivity.
-  - [ ] Operator disconnect stops tunnel immediately.
+  - [x] Operator disconnect stops tunnel immediately.
 - Security:
-  - [ ] Client-to-client blocked.
+  - [x] Client-to-client blocked.
-  - [ ] Only engine IP reachable; per-agent ACL enforces allowed ports.
+  - [x] Only engine IP reachable; per-agent ACL enforces allowed ports.
-  - [ ] Token enforcement blocks stale/unauthorized sessions.
+  - [x] Token enforcement blocks stale/unauthorized sessions.
 - Resilience:
-  - [ ] Restart engine: WireGuard server starts; no orphaned routes.
+  - [x] Restart engine: WireGuard server starts; no orphaned routes.
-  - [ ] Restart agent: adapter persists; tunnel stays down until requested.
+  - [x] Restart agent: adapter persists; tunnel stays down until requested.
 - Logging/audit:
-  - [ ] Connect/disconnect/idle/stop reasons recorded in reverse_tunnel.log (Engine/Agent) and Device Activity.
+  - [x] Connect/disconnect/idle/stop reasons recorded in `VPN_Tunnel/tunnel.log` (Engine/Agent) and Device Activity; shell I/O recorded in `VPN_Tunnel/remote_shell.log`.
 - Checkpoint tests:
-  - [ ] Run the above matrix; gather logs for operator review before final commit.
+  - [x] Run the above matrix; gather logs for operator review before final commit.
 
 ## Linux (Deferred) — Do Not Implement Yet
 - When greenlit, mirror the structure above for Linux: