coder · ethanndickson · Jul 24, 2025
diff --git a/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift b/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift
@@ -26,7 +26,6 @@ struct DesktopApp: App {
             SettingsView<CoderVPNService>()
                 .environmentObject(appDelegate.vpn)
                 .environmentObject(appDelegate.state)
-                .environmentObject(appDelegate.helper)
                 .environmentObject(appDelegate.autoUpdater)
         }
         .windowResizability(.contentSize)
@@ -48,13 +47,11 @@ class AppDelegate: NSObject, NSApplicationDelegate {
     let fileSyncDaemon: MutagenDaemon
     let urlHandler: URLHandler
     let notifDelegate: NotifDelegate
-    let helper: HelperService
     let autoUpdater: UpdaterService
 
     override init() {
         notifDelegate = NotifDelegate()
         vpn = CoderVPNService()
-        helper = HelperService()
         autoUpdater = UpdaterService()
         let state = AppState(onChange: vpn.configureTunnelProviderProtocol)
         vpn.onStart = {
@@ -95,10 +92,16 @@ class AppDelegate: NSObject, NSApplicationDelegate {
             image: "MenuBarIcon",
             onAppear: {
                 // If the VPN is enabled, it's likely the token isn't expired
-                guard self.vpn.state != .connected, self.state.hasSession else { return }
                 Task { @MainActor in
+                    guard self.vpn.state != .connected, self.state.hasSession else { return }
                     await self.state.handleTokenExpiry()
                 }
+                // If the Helper is pending approval, we should check if it's
+                // been approved when the tray is opened.
+                Task { @MainActor in
+                    guard self.vpn.state == .failed(.helperError(.requiresApproval)) else { return }
+                    self.vpn.refreshHelperState()
+                }
             }, content: {
                 VPNMenu<CoderVPNService, MutagenDaemon>().frame(width: 256)
                     .environmentObject(self.vpn)
@@ -119,6 +122,7 @@ class AppDelegate: NSObject, NSApplicationDelegate {
             if await !vpn.loadNetworkExtensionConfig() {
                 state.reconfigure()
             }
+            await vpn.setupHelper()
         }
     }
 

diff --git a/Coder-Desktop/Coder-Desktop/HelperService.swift b/Coder-Desktop/Coder-Desktop/HelperService.swift
@@ -1,54 +1,84 @@
 import os
 import ServiceManagement
 
-// Whilst the GUI app installs the helper, the System Extension communicates
-// with it over XPC
-@MainActor
-class HelperService: ObservableObject {
-    private let logger = Logger(subsystem: Bundle.main.bundleIdentifier!, category: "HelperService")
-    let plistName = "com.coder.Coder-Desktop.Helper.plist"
-    @Published var state: HelperState = .uninstalled {
-        didSet {
-            logger.info("helper daemon state set: \(self.state.description, privacy: .public)")
-        }
-    }
+extension CoderVPNService {
+    var plistName: String { "com.coder.Coder-Desktop.Helper.plist" }
 
-    init() {
-        update()
+    func refreshHelperState() {
+        let daemon = SMAppService.daemon(plistName: plistName)
+        helperState = HelperState(status: daemon.status)
     }
 
-    func update() {
-        let daemon = SMAppService.daemon(plistName: plistName)
-        state = HelperState(status: daemon.status)
+    func setupHelper() async {
+        refreshHelperState()
+        switch helperState {
+        case .uninstalled, .failed:
+            await installHelper()
+        case .installed:
+            uninstallHelper()
+            await installHelper()
+        case .requiresApproval, .installing:
+            break
+        }
     }
 
-    func install() {
-        let daemon = SMAppService.daemon(plistName: plistName)
-        do {
-            try daemon.register()
-        } catch let error as NSError {
-            self.state = .failed(.init(error: error))
-        } catch {
-            state = .failed(.unknown(error.localizedDescription))
+    private func installHelper() async {
+        // Worst case, this setup takes a few seconds. We'll show a loading
+        // indicator in the meantime.
+        helperState = .installing
+        var lastUnknownError: Error?
+        // Registration may fail with a permissions error if it was
+        // just unregistered, so we retry a few times.
+        for _ in 0 ... 10 {
+            let daemon = SMAppService.daemon(plistName: plistName)
+            do {
+                try daemon.register()
+                helperState = HelperState(status: daemon.status)
+                return
+            } catch {
+                if daemon.status == .requiresApproval {
+                    helperState = .requiresApproval
+                    return
+                }
+                let helperError = HelperError(error: error as NSError)
+                switch helperError {
+                case .alreadyRegistered:
+                    helperState = .installed
+                    return
+                case .launchDeniedByUser, .invalidSignature:
+                    // Something weird happened, we should update the UI
+                    helperState = .failed(helperError)
+                    return
+                case .unknown:
+                    // Likely intermittent permissions error, we'll retry
+                    lastUnknownError = error
+                    logger.warning("failed to register helper: \(helperError.localizedDescription)")
+                }
+
+                // Short delay before retrying
+                try? await Task.sleep(for: .milliseconds(500))
+            }
         }
-        state = HelperState(status: daemon.status)
+        // Give up, update the UI with the error
+        helperState = .failed(.unknown(lastUnknownError?.localizedDescription ?? "Unknown"))
     }
 
-    func uninstall() {
+    private func uninstallHelper() {
         let daemon = SMAppService.daemon(plistName: plistName)
         do {
             try daemon.unregister()
         } catch let error as NSError {
-            self.state = .failed(.init(error: error))
+            helperState = .failed(.init(error: error))
         } catch {
-            state = .failed(.unknown(error.localizedDescription))
+            helperState = .failed(.unknown(error.localizedDescription))
         }
-        state = HelperState(status: daemon.status)
+        helperState = HelperState(status: daemon.status)
     }
 }
 
 enum HelperState: Equatable {
     case uninstalled
+    case installing
     case installed
     case requiresApproval
     case failed(HelperError)
@@ -57,6 +87,8 @@ enum HelperState: Equatable {
         switch self {
         case .uninstalled:
             "Uninstalled"
+        case .installing:
+            "Installing"
         case .installed:
             "Installed"
         case .requiresApproval:

diff --git a/Coder-Desktop/Coder-Desktop/Preview Content/PreviewVPN.swift b/Coder-Desktop/Coder-Desktop/Preview Content/PreviewVPN.swift
@@ -81,5 +81,7 @@ final class PreviewVPN: Coder_Desktop.VPNService {
         state = .connecting
     }
 
+    func updateHelperState() {}
+
     var startWhenReady: Bool = false
 }
diff --git a/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift b/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
@@ -36,6 +36,7 @@ enum VPNServiceError: Error, Equatable {
     case internalError(String)
     case systemExtensionError(SystemExtensionState)
     case networkExtensionError(NetworkExtensionState)
+    case helperError(HelperState)
 
     var description: String {
         switch self {
@@ -45,6 +46,8 @@ enum VPNServiceError: Error, Equatable {
             "SystemExtensionError: \(state.description)"
         case let .networkExtensionError(state):
             "NetworkExtensionError: \(state.description)"
+        case let .helperError(state):
+            "HelperError: \(state.description)"
         }
     }
 
@@ -67,6 +70,13 @@ final class CoderVPNService: NSObject, VPNService {
     @Published var sysExtnState: SystemExtensionState = .uninstalled
     @Published var neState: NetworkExtensionState = .unconfigured
     var state: VPNServiceState {
+        // The ordering here is important. The button to open the settings page
+        // where the helper is approved is a no-op if the user has a settings
+        // window on the page where the system extension is approved.
+        // So, we want to ensure the helper settings button is clicked first.
+        guard helperState == .installed else {
+            return .failed(.helperError(helperState))
+        }
         guard sysExtnState == .installed else {
             return .failed(.systemExtensionError(sysExtnState))
         }
@@ -80,6 +90,8 @@ final class CoderVPNService: NSObject, VPNService {
         return tunnelState
     }
 
+    @Published var helperState: HelperState = .uninstalled
+
     @Published var progress: VPNProgress = .init(stage: .initial, downloadProgress: nil)
 
     @Published var menuState: VPNMenuState = .init()
@@ -107,6 +119,14 @@ final class CoderVPNService: NSObject, VPNService {
             return
         }
 
+        // We have to manually fetch the helper state,
+        // and we don't want to start the VPN
+        // if the helper is not ready.
+        refreshHelperState()
+        if helperState != .installed {
+            return
+        }
+
         menuState.clear()
         await startTunnel()
         logger.debug("network extension enabled")

diff --git a/Coder-Desktop/Coder-Desktop/Views/Settings/ExperimentalTab.swift b/Coder-Desktop/Coder-Desktop/Views/Settings/ExperimentalTab.swift
diff --git a/Coder-Desktop/Coder-Desktop/Views/Settings/HelperSection.swift b/Coder-Desktop/Coder-Desktop/Views/Settings/HelperSection.swift
diff --git a/Coder-Desktop/Coder-Desktop/Views/Settings/Settings.swift b/Coder-Desktop/Coder-Desktop/Views/Settings/Settings.swift
@@ -13,11 +13,6 @@ struct SettingsView<VPN: VPNService>: View {
                 .tabItem {
                     Label("Network", systemImage: "dot.radiowaves.left.and.right")
                 }.tag(SettingsTab.network)
-            ExperimentalTab()
-                .tabItem {
-                    Label("Experimental", systemImage: "gearshape.2")
-                }.tag(SettingsTab.experimental)
-
         }.frame(width: 600)
             .frame(maxHeight: 500)
             .scrollContentBackground(.hidden)
@@ -28,5 +23,4 @@ struct SettingsView<VPN: VPNService>: View {
 enum SettingsTab: Int {
     case general
     case network
-    case experimental
 }
diff --git a/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenu.swift b/Coder-Desktop/Coder-Desktop/Views/VPN/VPNMenu.swift
@@ -124,7 +124,11 @@ struct VPNMenu<VPN: VPNService, FS: FileSyncDaemon>: View {
                 // Prevent starting the VPN before the user has approved the system extension.
                 vpn.state == .failed(.systemExtensionError(.needsUserApproval)) ||
                 // Prevent starting the VPN without a VPN configuration.
-                vpn.state == .failed(.networkExtensionError(.unconfigured))
+                vpn.state == .failed(.networkExtensionError(.unconfigured)) ||
+                // Prevent starting the VPN before the Helper is approved
+                vpn.state == .failed(.helperError(.requiresApproval)) ||
+                // Prevent starting the VPN before the Helper is installed
+                vpn.state == .failed(.helperError(.installing))
         )
     }
 }