refactor: unify gateway connectivity state

apps/macos/Sources/Clawdbot/ControlChannel.swift

@@ -87,15 +87,7 @@ final class ControlChannel {
 
     func configure() async {
         self.logger.info("control channel configure mode=local")
-        self.state = .connecting
+        await self.refreshEndpoint(reason: "configure")
-        do {
-            try await GatewayConnection.shared.refresh()
-            self.state = .connected
-            PresenceReporter.shared.sendImmediate(reason: "connect")
-        } catch {
-            let message = self.friendlyGatewayMessage(error)
-            self.state = .degraded(message)
-        }
     }
 
     func configure(mode: Mode = .local) async throws {
@@ -111,7 +103,7 @@ final class ControlChannel {
                         "target=\(target, privacy: .public) identitySet=\(idSet, privacy: .public)")
                 self.state = .connecting
                 _ = try await GatewayEndpointStore.shared.ensureRemoteControlTunnel()
-                await self.configure()
+                await self.refreshEndpoint(reason: "configure")
             } catch {
                 self.state = .degraded(error.localizedDescription)
                 throw error
@@ -119,6 +111,19 @@ final class ControlChannel {
         }
     }
 
+    func refreshEndpoint(reason: String) async {
+        self.logger.info("control channel refresh endpoint reason=\(reason, privacy: .public)")
+        self.state = .connecting
+        do {
+            try await self.establishGatewayConnection()
+            self.state = .connected
+            PresenceReporter.shared.sendImmediate(reason: "connect")
+        } catch {
+            let message = self.friendlyGatewayMessage(error)
+            self.state = .degraded(message)
+        }
+    }
+
     func disconnect() async {
         await GatewayConnection.shared.shutdown()
         self.state = .disconnected
@@ -275,18 +280,28 @@ final class ControlChannel {
                 }
             }
 
-            do {
+            await self.refreshEndpoint(reason: "recovery:\(reasonText)")
-                try await GatewayConnection.shared.refresh()
+            if case .connected = self.state {
                 self.logger.info("control channel recovery finished")
-            } catch {
+            } else if case let .degraded(message) = self.state {
-                self.logger.error(
+                self.logger.error("control channel recovery failed \(message, privacy: .public)")
-                    "control channel recovery failed \(error.localizedDescription, privacy: .public)")
             }
 
             self.recoveryTask = nil
         }
     }
 
+    private func establishGatewayConnection(timeoutMs: Int = 5000) async throws {
+        try await GatewayConnection.shared.refresh()
+        let ok = try await GatewayConnection.shared.healthOK(timeoutMs: timeoutMs)
+        if ok == false {
+            throw NSError(
+                domain: "Gateway",
+                code: 0,
+                userInfo: [NSLocalizedDescriptionKey: "gateway health not ok"])
+        }
+    }
+
     func sendSystemEvent(_ text: String, params: [String: AnyHashable] = [:]) async throws {
         var merged = params
         merged["text"] = AnyHashable(text)

apps/macos/Sources/Clawdbot/GatewayConnectivityCoordinator.swift

@@ -0,0 +1,63 @@
+import Foundation
+import Observation
+import OSLog
+
+@MainActor
+@Observable
+final class GatewayConnectivityCoordinator {
+    static let shared = GatewayConnectivityCoordinator()
+
+    private let logger = Logger(subsystem: "com.clawdbot", category: "gateway.connectivity")
+    private var endpointTask: Task<Void, Never>?
+    private var lastResolvedURL: URL?
+
+    private(set) var endpointState: GatewayEndpointState?
+    private(set) var resolvedURL: URL?
+    private(set) var resolvedMode: AppState.ConnectionMode?
+    private(set) var resolvedHostLabel: String?
+
+    private init() {
+        self.start()
+    }
+
+    func start() {
+        guard self.endpointTask == nil else { return }
+        self.endpointTask = Task { [weak self] in
+            guard let self else { return }
+            let stream = await GatewayEndpointStore.shared.subscribe()
+            for await state in stream {
+                await MainActor.run { self.handleEndpointState(state) }
+            }
+        }
+    }
+
+    var localEndpointHostLabel: String? {
+        guard self.resolvedMode == .local, let url = self.resolvedURL else { return nil }
+        return Self.hostLabel(for: url)
+    }
+
+    private func handleEndpointState(_ state: GatewayEndpointState) {
+        self.endpointState = state
+        switch state {
+        case let .ready(mode, url, _, _):
+            self.resolvedMode = mode
+            self.resolvedURL = url
+            self.resolvedHostLabel = Self.hostLabel(for: url)
+            let urlChanged = self.lastResolvedURL?.absoluteString != url.absoluteString
+            if urlChanged {
+                self.lastResolvedURL = url
+                Task { await ControlChannel.shared.refreshEndpoint(reason: "endpoint changed") }
+            }
+        case let .connecting(mode, _):
+            self.resolvedMode = mode
+        case let .unavailable(mode, _):
+            self.resolvedMode = mode
+        }
+    }
+
+    private static func hostLabel(for url: URL) -> String {
+        let host = url.host ?? url.absoluteString
+        if let port = url.port { return "\(host):\(port)" }
+        return host
+    }
+}

apps/macos/Sources/Clawdbot/GatewayEndpointStore.swift

@@ -68,6 +68,7 @@ actor GatewayEndpointStore {
                     env: ProcessInfo.processInfo.environment)
                 let customBindHost = GatewayEndpointStore.resolveGatewayCustomBindHost(root: root)
                 let tailscaleIP = await MainActor.run { TailscaleService.shared.tailscaleIP }
+                    ?? TailscaleService.fallbackTailnetIPv4()
                 return GatewayEndpointStore.resolveLocalGatewayHost(
                     bindMode: bind,
                     customBindHost: customBindHost,
@@ -487,6 +488,7 @@ actor GatewayEndpointStore {
         guard currentHost == "127.0.0.1" || currentHost == "localhost" else { return nil }
 
         let tailscaleIP = await MainActor.run { TailscaleService.shared.tailscaleIP }
+            ?? TailscaleService.fallbackTailnetIPv4()
         guard let tailscaleIP, !tailscaleIP.isEmpty else { return nil }
 
         let scheme = GatewayEndpointStore.resolveGatewayScheme(

apps/macos/Sources/Clawdbot/HealthStore.swift

@@ -235,8 +235,8 @@ final class HealthStore {
             let lower = error.lowercased()
             if lower.contains("connection refused") {
                 let port = GatewayEnvironment.gatewayPort()
-                return "The gateway control port (127.0.0.1:\(port)) isn’t listening — " +
+                let host = GatewayConnectivityCoordinator.shared.localEndpointHostLabel ?? "127.0.0.1:\(port)"
-                    "restart Clawdbot to bring it back."
+                return "The gateway control port (\(host)) isn’t listening — restart Clawdbot to bring it back."
             }
             if lower.contains("timeout") {
                 return "Timed out waiting for the control server; the gateway may be crashed or still starting."

apps/macos/Sources/Clawdbot/MenuBar.swift

@@ -13,6 +13,7 @@ struct ClawdbotApp: App {
     private let gatewayManager = GatewayProcessManager.shared
     private let controlChannel = ControlChannel.shared
     private let activityStore = WorkActivityStore.shared
+    private let connectivityCoordinator = GatewayConnectivityCoordinator.shared
     @State private var statusItem: NSStatusItem?
     @State private var isMenuPresented = false
     @State private var isPanelVisible = false

apps/macos/Sources/Clawdbot/MenuSessionsInjector.swift

@@ -469,7 +469,7 @@ extension MenuSessionsInjector {
             }
         case .local:
             platform = "local"
-            host = "127.0.0.1:\(port)"
+            host = GatewayConnectivityCoordinator.shared.localEndpointHostLabel ?? "127.0.0.1:\(port)"
         case .unconfigured:
             platform = nil
             host = nil

apps/macos/Sources/Clawdbot/TailscaleService.swift

@@ -103,6 +103,7 @@ final class TailscaleService {
     }
 
     func checkTailscaleStatus() async {
+        let previousIP = self.tailscaleIP
         self.isInstalled = self.checkAppInstallation()
         if !self.isInstalled {
             self.isRunning = false
@@ -147,6 +148,10 @@ final class TailscaleService {
             self.statusError = nil
             self.logger.info("Tailscale interface IP detected (fallback) ip=\(fallback, privacy: .public)")
         }
+
+        if previousIP != self.tailscaleIP {
+            await GatewayEndpointStore.shared.refresh()
+        }
     }
 
     func openTailscaleApp() {
@@ -214,4 +219,8 @@ final class TailscaleService {
 
         return nil
     }
+
+    nonisolated static func fallbackTailnetIPv4() -> String? {
+        Self.detectTailnetIPv4()
+    }
 }