diff --git a/apps/macos/Sources/Clawdis/GatewayChannel.swift b/apps/macos/Sources/Clawdis/GatewayChannel.swift
index f12a0f103..b85cf54d0 100644
--- a/apps/macos/Sources/Clawdis/GatewayChannel.swift
+++ b/apps/macos/Sources/Clawdis/GatewayChannel.swift
@@ -23,6 +23,8 @@ private actor GatewayChannelActor {
     private var task: URLSessionWebSocketTask?
     private var pending: [String: CheckedContinuation<GatewayFrame, Error>] = [:]
     private var connected = false
+    private var isConnecting = false
+    private var connectWaiters: [CheckedContinuation<Void, Error>] = []
     private var url: URL
     private var token: String?
     private let session = URLSession(configuration: .default)
@@ -68,6 +70,15 @@ private actor GatewayChannelActor {
 
     func connect() async throws {
         if self.connected, self.task?.state == .running { return }
+        if self.isConnecting {
+            try await withCheckedThrowingContinuation { cont in
+                self.connectWaiters.append(cont)
+            }
+            return
+        }
+        self.isConnecting = true
+        defer { self.isConnecting = false }
+
         self.task?.cancel(with: .goingAway, reason: nil)
         self.task = self.session.webSocketTask(with: self.url)
         self.task?.resume()
@@ -75,12 +86,26 @@ private actor GatewayChannelActor {
             try await self.sendHello()
         } catch {
             let wrapped = self.wrap(error, context: "connect to gateway @ \(self.url.absoluteString)")
+            self.connected = false
+            self.task?.cancel(with: .goingAway, reason: nil)
+            let waiters = self.connectWaiters
+            self.connectWaiters.removeAll()
+            for waiter in waiters {
+                waiter.resume(throwing: wrapped)
+            }
+            self.logger.error("gateway ws connect failed \(wrapped.localizedDescription, privacy: .public)")
             throw wrapped
         }
         self.listen()
         self.connected = true
         self.backoffMs = 500
         self.lastSeq = nil
+
+        let waiters = self.connectWaiters
+        self.connectWaiters.removeAll()
+        for waiter in waiters {
+            waiter.resume(returning: ())
+        }
     }
 
     private func sendHello() async throws {
@@ -141,7 +166,7 @@ private actor GatewayChannelActor {
             return
         }
         if let err = try? decoder.decode(HelloError.self, from: data) {
-            let reason = err.reason ?? "unknown"
+            let reason = err.reason
             // Log and throw a detailed error so UI can surface token/hello issues.
             self.logger.error("gateway hello-error: \(reason, privacy: .public)")
             throw NSError(
@@ -284,6 +309,13 @@ private actor GatewayChannelActor {
                     try await self.task?.send(.data(data))
                 } catch {
                     self.pending.removeValue(forKey: id)
+                    // Treat send failures as a broken socket: mark disconnected and trigger reconnect.
+                    self.connected = false
+                    self.task?.cancel(with: .goingAway, reason: nil)
+                    Task { [weak self] in
+                        guard let self else { return }
+                        await self.scheduleReconnect()
+                    }
                     cont.resume(throwing: self.wrap(error, context: "gateway send \(method)"))
                 }
             }