diff --git a/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift b/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift
index de12c6e..73589d3 100644
--- a/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift
+++ b/Coder-Desktop/Coder-Desktop/Coder_DesktopApp.swift
@@ -42,17 +42,16 @@ struct DesktopApp: App {
 @MainActor
 class AppDelegate: NSObject, NSApplicationDelegate {
     private var logger = Logger(subsystem: Bundle.main.bundleIdentifier!, category: "app-delegate")
-    private var menuBar: MenuBarController?
+    var menuBar: MenuBarController?
     let vpn: CoderVPNService
     let state: AppState
     let fileSyncDaemon: MutagenDaemon
     let urlHandler: URLHandler
-    let notifDelegate: NotifDelegate
     let helper: HelperService
     let autoUpdater: UpdaterService
 
     override init() {
-        notifDelegate = NotifDelegate()
+        AppDelegate.registerNotificationCategories()
         vpn = CoderVPNService()
         helper = HelperService()
         autoUpdater = UpdaterService()
@@ -79,8 +78,9 @@ class AppDelegate: NSObject, NSApplicationDelegate {
         }
         self.fileSyncDaemon = fileSyncDaemon
         urlHandler = URLHandler(state: state, vpn: vpn)
+        super.init()
         // `delegate` is weak
-        UNUserNotificationCenter.current().delegate = notifDelegate
+        UNUserNotificationCenter.current().delegate = self
     }
 
     func applicationDidFinishLaunching(_: Notification) {
@@ -161,7 +161,11 @@ class AppDelegate: NSObject, NSApplicationDelegate {
         do { try urlHandler.handle(url) } catch let handleError {
             Task {
                 do {
-                    try await sendNotification(title: "Failed to handle link", body: handleError.description)
+                    try await sendNotification(
+                        title: "Failed to handle link",
+                        body: handleError.description,
+                        category: .uriFailure
+                    )
                 } catch let notifError {
                     logger.error("Failed to send notification (\(handleError.description)): \(notifError)")
                 }
diff --git a/Coder-Desktop/Coder-Desktop/Notifications.swift b/Coder-Desktop/Coder-Desktop/Notifications.swift
index 44a2afb..e3ffcf5 100644
--- a/Coder-Desktop/Coder-Desktop/Notifications.swift
+++ b/Coder-Desktop/Coder-Desktop/Notifications.swift
@@ -1,8 +1,23 @@
 import UserNotifications
 
-class NotifDelegate: NSObject, UNUserNotificationCenterDelegate {
-    override init() {
-        super.init()
+extension AppDelegate: UNUserNotificationCenterDelegate {
+    static func registerNotificationCategories() {
+        let vpnFailure = UNNotificationCategory(
+            identifier: NotificationCategory.vpnFailure.rawValue,
+            actions: [],
+            intentIdentifiers: [],
+            options: []
+        )
+
+        let uriFailure = UNNotificationCategory(
+            identifier: NotificationCategory.uriFailure.rawValue,
+            actions: [],
+            intentIdentifiers: [],
+            options: []
+        )
+
+        UNUserNotificationCenter.current()
+            .setNotificationCategories([vpnFailure, uriFailure])
     }
 
     // This function is required for notifications to appear as banners whilst the app is running.
@@ -13,9 +28,28 @@ class NotifDelegate: NSObject, UNUserNotificationCenterDelegate {
     ) async -> UNNotificationPresentationOptions {
         [.banner]
     }
+
+    nonisolated func userNotificationCenter(
+        _: UNUserNotificationCenter,
+        didReceive response: UNNotificationResponse,
+        withCompletionHandler completionHandler: @escaping () -> Void
+    ) {
+        let category = response.notification.request.content.categoryIdentifier
+        let action = response.actionIdentifier
+        switch (category, action) {
+        // Default action for VPN failure notification
+        case (NotificationCategory.vpnFailure.rawValue, UNNotificationDefaultActionIdentifier):
+            Task { @MainActor in
+                self.menuBar?.menuBarExtra.toggleVisibility()
+            }
+        default:
+            break
+        }
+        completionHandler()
+    }
 }
 
-func sendNotification(title: String, body: String) async throws {
+func sendNotification(title: String, body: String, category: NotificationCategory) async throws {
     let nc = UNUserNotificationCenter.current()
     let granted = try await nc.requestAuthorization(options: [.alert, .badge])
     guard granted else {
@@ -24,5 +58,11 @@ func sendNotification(title: String, body: String) async throws {
     let content = UNMutableNotificationContent()
     content.title = title
     content.body = body
+    content.categoryIdentifier = category.rawValue
     try await nc.add(.init(identifier: UUID().uuidString, content: content, trigger: nil))
 }
+
+enum NotificationCategory: String {
+    case vpnFailure = "VPN_FAILURE"
+    case uriFailure = "URI_FAILURE"
+}
diff --git a/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift b/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
index 224174a..5f461ff 100644
--- a/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
+++ b/Coder-Desktop/Coder-Desktop/VPN/VPNService.swift
@@ -61,6 +61,18 @@ final class CoderVPNService: NSObject, VPNService {
             if tunnelState == .connecting {
                 progress = .init(stage: .initial, downloadProgress: nil)
             }
+            if case let .failed(tunnelError) = tunnelState, tunnelState != oldValue {
+                Task {
+                    do {
+                        try await sendNotification(
+                            title: "Coder Connect has failed!",
+                            body: tunnelError.description, category: .vpnFailure
+                        )
+                    } catch let notifError {
+                        logger.error("Failed to send notification (\(tunnelError.description)): \(notifError)")
+                    }
+                }
+            }
         }
     }
 
diff --git a/Coder-Desktop/project.yml b/Coder-Desktop/project.yml
index 166a157..dc5bc7b 100644
--- a/Coder-Desktop/project.yml
+++ b/Coder-Desktop/project.yml
@@ -98,7 +98,7 @@ packages:
     # - Set onAppear/disappear handlers.
     # The upstream repo has a purposefully limited API
     url: https://github.com/coder/fluid-menu-bar-extra
-    revision: 8e1d8b8
+    revision: afc9256
   KeychainAccess:
     url: https://github.com/kishikawakatsumi/KeychainAccess
     branch: e0c7eebc5a4465a3c4680764f26b7a61f567cdaf