diff --git a/apps/macos/Sources/Clawdis/AppState.swift b/apps/macos/Sources/Clawdis/AppState.swift
index 4706b5971..e13f82bf3 100644
--- a/apps/macos/Sources/Clawdis/AppState.swift
+++ b/apps/macos/Sources/Clawdis/AppState.swift
@@ -138,7 +138,7 @@ final class AppState: ObservableObject {
 
     init() {
         self.isPaused = UserDefaults.standard.bool(forKey: pauseDefaultsKey)
-        self.launchAtLogin = LaunchAgentManager.status()
+        self.launchAtLogin = false
         self.onboardingSeen = UserDefaults.standard.bool(forKey: "clawdis.onboardingSeen")
         self.debugPaneEnabled = UserDefaults.standard.bool(forKey: "clawdis.debugPaneEnabled")
         let savedVoiceWake = UserDefaults.standard.bool(forKey: swabbleEnabledKey)
@@ -189,6 +189,11 @@ final class AppState: ObservableObject {
         let storedPort = UserDefaults.standard.integer(forKey: webChatPortKey)
         self.webChatPort = storedPort > 0 ? storedPort : 18788
 
+        Task.detached(priority: .utility) { [weak self] in
+            let current = await LaunchAgentManager.status()
+            await MainActor.run { [weak self] in self?.launchAtLogin = current }
+        }
+
         if self.swabbleEnabled, !PermissionManager.voiceWakePermissionsGranted() {
             self.swabbleEnabled = false
         }
@@ -248,7 +253,9 @@ enum AppStateStore {
     static var isPausedFlag: Bool { UserDefaults.standard.bool(forKey: pauseDefaultsKey) }
 
     static func updateLaunchAtLogin(enabled: Bool) {
-        LaunchAgentManager.set(enabled: enabled, bundlePath: Bundle.main.bundlePath)
+        Task.detached(priority: .utility) {
+            await LaunchAgentManager.set(enabled: enabled, bundlePath: Bundle.main.bundlePath)
+        }
     }
 
     static var webChatEnabled: Bool {
diff --git a/apps/macos/Sources/Clawdis/Utilities.swift b/apps/macos/Sources/Clawdis/Utilities.swift
index 03af58a23..403a5768e 100644
--- a/apps/macos/Sources/Clawdis/Utilities.swift
+++ b/apps/macos/Sources/Clawdis/Utilities.swift
@@ -26,18 +26,18 @@ enum LaunchAgentManager {
             .appendingPathComponent("Library/LaunchAgents/com.steipete.clawdis.plist")
     }
 
-    static func status() -> Bool {
+    static func status() async -> Bool {
         guard FileManager.default.fileExists(atPath: self.plistURL.path) else { return false }
-        let result = self.runLaunchctl(["print", "gui/\(getuid())/\(launchdLabel)"])
+        let result = await self.runLaunchctl(["print", "gui/\(getuid())/\(launchdLabel)"])
         return result == 0
     }
 
-    static func set(enabled: Bool, bundlePath: String) {
+    static func set(enabled: Bool, bundlePath: String) async {
         if enabled {
             self.writePlist(bundlePath: bundlePath)
-            _ = self.runLaunchctl(["bootout", "gui/\(getuid())/\(launchdLabel)"])
-            _ = self.runLaunchctl(["bootstrap", "gui/\(getuid())", self.plistURL.path])
-            _ = self.runLaunchctl(["kickstart", "-k", "gui/\(getuid())/\(launchdLabel)"])
+            _ = await self.runLaunchctl(["bootout", "gui/\(getuid())/\(launchdLabel)"])
+            _ = await self.runLaunchctl(["bootstrap", "gui/\(getuid())", self.plistURL.path])
+            _ = await self.runLaunchctl(["kickstart", "-k", "gui/\(getuid())/\(launchdLabel)"])
         } else {
             // Disable autostart going forward but leave the current app running.
             // bootout would terminate the launchd job immediately (and crash the app if launched via agent).
@@ -84,15 +84,21 @@ enum LaunchAgentManager {
     }
 
     @discardableResult
-    private static func runLaunchctl(_ args: [String]) -> Int32 {
-        let process = Process()
-        process.launchPath = "/bin/launchctl"
-        process.arguments = args
-        process.standardOutput = Pipe()
-        process.standardError = Pipe()
-        try? process.run()
-        process.waitUntilExit()
-        return process.terminationStatus
+    private static func runLaunchctl(_ args: [String]) async -> Int32 {
+        await Task.detached(priority: .utility) { () -> Int32 in
+            let process = Process()
+            process.launchPath = "/bin/launchctl"
+            process.arguments = args
+            process.standardOutput = Pipe()
+            process.standardError = Pipe()
+            do {
+                try process.run()
+                process.waitUntilExit()
+                return process.terminationStatus
+            } catch {
+                return -1
+            }
+        }.value
     }
 }
 
diff --git a/apps/macos/Sources/Clawdis/WebChatWindow.swift b/apps/macos/Sources/Clawdis/WebChatWindow.swift
index a2753ee67..2dc647c2b 100644
--- a/apps/macos/Sources/Clawdis/WebChatWindow.swift
+++ b/apps/macos/Sources/Clawdis/WebChatWindow.swift
@@ -217,7 +217,7 @@ final class WebChatTunnel {
             throw NSError(domain: "WebChat", code: 3, userInfo: [NSLocalizedDescriptionKey: "remote not configured"])
         }
 
-        let localPort = try Self.findPort(preferred: preferredLocalPort)
+        let localPort = try await Self.findPort(preferred: preferredLocalPort)
         var args: [String] = [
             "-o", "BatchMode=yes",
             "-o", "IdentitiesOnly=yes",
@@ -250,19 +250,35 @@ final class WebChatTunnel {
         return WebChatTunnel(process: process, localPort: localPort)
     }
 
-    private static func findPort(preferred: UInt16?) throws -> UInt16 {
-        if let preferred {
-            if Self.portIsFree(preferred) { return preferred }
+    private static func findPort(preferred: UInt16?) async throws -> UInt16 {
+        if let preferred, Self.portIsFree(preferred) { return preferred }
+
+        return try await withCheckedThrowingContinuation { cont in
+            let queue = DispatchQueue(label: "com.steipete.clawdis.webchat.port", qos: .utility)
+            do {
+                let listener = try NWListener(using: .tcp, on: .any)
+                listener.newConnectionHandler = { connection in connection.cancel() }
+                listener.stateUpdateHandler = { state in
+                    switch state {
+                    case .ready:
+                        if let port = listener.port?.rawValue {
+                            listener.stateUpdateHandler = nil
+                            listener.cancel()
+                            cont.resume(returning: port)
+                        }
+                    case let .failed(error):
+                        listener.stateUpdateHandler = nil
+                        listener.cancel()
+                        cont.resume(throwing: error)
+                    default:
+                        break
+                    }
+                }
+                listener.start(queue: queue)
+            } catch {
+                cont.resume(throwing: error)
+            }
         }
-        let listener = try NWListener(using: .tcp, on: .any)
-        listener.start(queue: .main)
-        while listener.port == nil {
-            RunLoop.current.run(mode: .default, before: Date().addingTimeInterval(0.05))
-        }
-        let port = listener.port?.rawValue
-        listener.cancel()
-        guard let port else { throw NSError(domain: "WebChat", code: 4, userInfo: [NSLocalizedDescriptionKey: "no port"])}
-        return port
     }
 
     private static func portIsFree(_ port: UInt16) -> Bool {