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feat: add troubleshooting tab and improve extension management
- Add new Troubleshooting tab to settings with system/network extension controls - Implement extension uninstallation and granular state management - Add "Stop VPN on Quit" setting to control VPN behavior when app closes - Improve error handling for extension operations - Add comprehensive status reporting for troubleshooting 🤖 Generated with [Claude Code](https://claude.ai/code) Co-Authored-By: Claude <noreply@anthropic.com> Change-Id: Id8327b1c9cd4cc2c4946edd0c8e93cab9a005315 Signed-off-by: Thomas Kosiewski <tk@coder.com>
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‎CLAUDE.md

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@@ -0,0 +1,22 @@
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# Coder Desktop Development Guide
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## Build & Test Commands
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- Build Xcode project: `make`
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- Format Swift files: `make fmt`
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- Lint Swift files: `make lint`
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- Run all tests: `make test`
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- Run specific test class: `xcodebuild test -project "Coder Desktop/Coder Desktop.xcodeproj" -scheme "Coder Desktop" -only-testing:"Coder DesktopTests/AgentsTests"`
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- Run specific test method: `xcodebuild test -project "Coder Desktop/Coder Desktop.xcodeproj" -scheme "Coder Desktop" -only-testing:"Coder DesktopTests/AgentsTests/agentsWhenVPNOff"`
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- Generate Swift from proto: `make proto`
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- Watch for project changes: `make watch-gen`
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## Code Style Guidelines
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- Use Swift 6.0 for development
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- Follow SwiftFormat and SwiftLint rules
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- Use Swift's Testing framework for tests (`@Test`, `#expect` directives)
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- Group files logically (Views, Models, Extensions)
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- Use environment objects for dependency injection
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- Prefer async/await over completion handlers
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- Use clear, descriptive naming for functions and variables
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- Implement proper error handling with Swift's throwing functions
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- Tests should use descriptive names reflecting what they're testing

‎Coder Desktop/Coder Desktop/Coder_DesktopApp.swift

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@@ -49,6 +49,13 @@ class AppDelegate: NSObject, NSApplicationDelegate {
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name: .NEVPNStatusDidChange,
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object: nil
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)
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// Subscribe to reconfiguration requests
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NotificationCenter.default.addObserver(
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self,
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selector: #selector(networkExtensionNeedsReconfiguration(_:)),
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name: .networkExtensionNeedsReconfiguration,
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object: nil
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)
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Task {
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// If there's no NE config, but the user is logged in, such as
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// from a previous install, then we need to reconfigure.
@@ -82,9 +89,27 @@ extension AppDelegate {
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vpn.vpnDidUpdate(connection)
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menuBar?.vpnDidUpdate(connection)
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}
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@objc private func networkExtensionNeedsReconfiguration(_: Notification) {
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// Check if we have a session
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if state.hasSession {
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// Reconfigure the network extension with full credentials
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state.reconfigure()
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} else {
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// No valid session, the user likely needs to log in again
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// Show the login window
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NSApp.sendAction(#selector(NSApp.showLoginWindow), to: nil, from: nil)
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}
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}
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}
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@MainActor
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func appActivate() {
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NSApp.activate()
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}
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extension NSApplication {
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@objc func showLoginWindow() {
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NSApp.sendAction(#selector(NSWindowController.showWindow(_:)), to: nil, from: Windows.login.rawValue)
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}
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}

‎Coder Desktop/Coder Desktop/Preview Content/PreviewVPN.swift

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@@ -26,11 +26,15 @@ final class PreviewVPN: Coder_Desktop.VPNService {
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UUID(): Agent(id: UUID(), name: "dev", status: .off, hosts: ["asdf.coder"], wsName: "example",
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wsID: UUID()),
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], workspaces: [:])
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@Published var sysExtnState: SystemExtensionState = .installed
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@Published var neState: NetworkExtensionState = .enabled
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let shouldFail: Bool
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let longError = "This is a long error to test the UI with long error messages"
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init(shouldFail: Bool = false) {
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init(shouldFail: Bool = false, extensionInstalled: Bool = true, networkExtensionEnabled: Bool = true) {
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self.shouldFail = shouldFail
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sysExtnState = extensionInstalled ? .installed : .uninstalled
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neState = networkExtensionEnabled ? .enabled : .disabled
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}
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var startTask: Task<Void, Never>?
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func configureTunnelProviderProtocol(proto _: NETunnelProviderProtocol?) {
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state = .connecting
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}
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func uninstall() async -> Bool {
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// Simulate uninstallation with a delay
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do {
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try await Task.sleep(for: .seconds(2))
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} catch {
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return false
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}
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if !shouldFail {
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sysExtnState = .uninstalled
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return true
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}
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return false
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}
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func installExtension() async {
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// Simulate installation with a delay
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do {
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try await Task.sleep(for: .seconds(2))
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sysExtnState = if !shouldFail {
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.installed
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} else {
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.failed("Failed to install extension")
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}
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} catch {
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sysExtnState = .failed("Installation was interrupted")
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}
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}
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func disableExtension() async -> Bool {
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// Simulate disabling with a delay
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do {
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try await Task.sleep(for: .seconds(1))
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} catch {
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return false
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}
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if !shouldFail {
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neState = .disabled
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state = .disabled
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return true
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} else {
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neState = .failed("Failed to disable network extension")
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return false
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}
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}
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func enableExtension() async -> Bool {
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// Simulate enabling with a delay
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do {
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try await Task.sleep(for: .seconds(1))
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} catch {
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return false
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}
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if !shouldFail {
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neState = .enabled
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state = .disabled // Just disabled, not connected yet
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return true
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} else {
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neState = .failed("Failed to enable network extension")
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return false
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}
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}
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}

‎Coder Desktop/Coder Desktop/State.swift

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@@ -8,7 +8,7 @@ class AppState: ObservableObject {
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let appId = Bundle.main.bundleIdentifier!
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// Stored in UserDefaults
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@Published private(set) var hasSession: Bool {
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@Published var hasSession: Bool {
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didSet {
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guard persistent else { return }
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UserDefaults.standard.set(hasSession, forKey: Keys.hasSession)

‎Coder Desktop/Coder Desktop/SystemExtension.swift

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@@ -81,6 +81,121 @@ extension CoderVPNService: SystemExtensionAsyncRecorder {
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OSSystemExtensionManager.shared.submitRequest(request)
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logger.info("submitted SystemExtension request with bundleID: \(bundleID)")
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}
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func deregisterSystemExtension() async -> Bool {
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logger.info("Starting network extension deregistration...")
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// Extension bundle identifier - must match what's used in the app
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let extensionBundleIdentifier = "com.coder.Coder-Desktop.VPN"
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return await withCheckedContinuation { continuation in
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// Create a task to handle the deregistration with timeout
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let timeoutTask = Task {
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// Set a timeout for the operation
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let timeoutInterval: TimeInterval = 30.0 // 30 seconds
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// Use a custom holder for the delegate to keep it alive
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// and store the result from the callback
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final class DelegateHolder {
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var delegate: DeregistrationDelegate?
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var result: Bool?
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}
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let holder = DelegateHolder()
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// Create the delegate with a completion handler
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let delegate = DeregistrationDelegate(completionHandler: { result in
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holder.result = result
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})
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holder.delegate = delegate
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// Create and submit the deactivation request
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let request = OSSystemExtensionRequest.deactivationRequest(
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forExtensionWithIdentifier: extensionBundleIdentifier,
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queue: .main
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)
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request.delegate = delegate
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// Submit the request on the main thread
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await MainActor.run {
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OSSystemExtensionManager.shared.submitRequest(request)
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}
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// Set up timeout using a separate task
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let timeoutDate = Date().addingTimeInterval(timeoutInterval)
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// Wait for completion or timeout
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while holder.result == nil, Date() < timeoutDate {
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// Sleep a bit before checking again (100ms)
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try? await Task.sleep(nanoseconds: 100_000_000)
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// Check for cancellation
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if Task.isCancelled {
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break
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}
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}
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// Handle the result
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if let result = holder.result {
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logger.info("System extension deregistration completed with result: \(result)")
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return result
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} else {
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logger.error("System extension deregistration timed out after \(timeoutInterval) seconds")
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return false
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}
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}
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// Use Task.detached to handle potential continuation issues
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Task.detached {
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let result = await timeoutTask.value
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continuation.resume(returning: result)
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}
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}
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}
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// A dedicated delegate class for system extension deregistration
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private class DeregistrationDelegate: NSObject, OSSystemExtensionRequestDelegate {
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private var logger = Logger(subsystem: Bundle.main.bundleIdentifier!, category: "vpn-deregistrar")
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private var completionHandler: (Bool) -> Void
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init(completionHandler: @escaping (Bool) -> Void) {
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self.completionHandler = completionHandler
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super.init()
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}
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func request(_: OSSystemExtensionRequest, didFinishWithResult result: OSSystemExtensionRequest.Result) {
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switch result {
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case .completed:
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logger.info("System extension was successfully deregistered")
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completionHandler(true)
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case .willCompleteAfterReboot:
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logger.info("System extension will be deregistered after reboot")
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completionHandler(true)
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@unknown default:
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logger.error("System extension deregistration completed with unknown result")
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completionHandler(false)
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}
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}
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func request(_: OSSystemExtensionRequest, didFailWithError error: Error) {
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logger.error("System extension deregistration failed: \(error.localizedDescription)")
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completionHandler(false)
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}
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func requestNeedsUserApproval(_: OSSystemExtensionRequest) {
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logger.info("System extension deregistration needs user approval")
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// We don't complete here, as we'll get another callback when approval is granted or denied
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}
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func request(
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_: OSSystemExtensionRequest,
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actionForReplacingExtension _: OSSystemExtensionProperties,
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withExtension _: OSSystemExtensionProperties
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) -> OSSystemExtensionRequest.ReplacementAction {
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logger.info("System extension replacement request")
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return .replace
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}
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}
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}
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/// A delegate for the OSSystemExtensionRequest that maps the callbacks to async calls on the

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