diff --git a/swift/apple/Firezone/Application/FirezoneApp.swift b/swift/apple/Firezone/Application/FirezoneApp.swift
index 4d62d6540..9f67b0138 100644
--- a/swift/apple/Firezone/Application/FirezoneApp.swift
+++ b/swift/apple/Firezone/Application/FirezoneApp.swift
@@ -26,7 +26,12 @@ struct FirezoneApp: App {
 
     #if os(macOS)
       self._askPermissionViewModel =
-        StateObject(wrappedValue: AskPermissionViewModel(tunnelStore: appStore.tunnelStore))
+        StateObject(
+          wrappedValue: AskPermissionViewModel(
+            tunnelStore: appStore.tunnelStore,
+            sessionNotificationHelper: SessionNotificationHelper(logger: appStore.logger, authStore: appStore.authStore)
+          )
+        )
       appDelegate.appStore = appStore
     #elseif os(iOS)
       self._appViewModel =
diff --git a/swift/apple/FirezoneKit/Sources/FirezoneKit/Features/AskPermissionView.swift b/swift/apple/FirezoneKit/Sources/FirezoneKit/Features/AskPermissionView.swift
index 1df142e6b..d355b9b05 100644
--- a/swift/apple/FirezoneKit/Sources/FirezoneKit/Features/AskPermissionView.swift
+++ b/swift/apple/FirezoneKit/Sources/FirezoneKit/Features/AskPermissionView.swift
@@ -11,6 +11,7 @@ import SwiftUI
 @MainActor
 public final class AskPermissionViewModel: ObservableObject {
   public var tunnelStore: TunnelStore
+  private var sessionNotificationHelper: SessionNotificationHelper
 
   private var cancellables: Set<AnyCancellable> = []
 
@@ -26,8 +27,11 @@ public final class AskPermissionViewModel: ObservableObject {
     }
   }
 
-  public init(tunnelStore: TunnelStore) {
+  @Published var needsNotificationDecision = false
+
+  public init(tunnelStore: TunnelStore, sessionNotificationHelper: SessionNotificationHelper) {
     self.tunnelStore = tunnelStore
+    self.sessionNotificationHelper = sessionNotificationHelper
 
     tunnelStore.$tunnelAuthStatus
       .filter { $0.isInitialized }
@@ -46,6 +50,23 @@ public final class AskPermissionViewModel: ObservableObject {
       }
       .store(in: &cancellables)
 
+    sessionNotificationHelper.$notificationDecision
+      .filter { $0.isInitialized }
+      .sink { [weak self] notificationDecision in
+        guard let self = self else { return }
+
+        Task {
+          await MainActor.run {
+            if case .notDetermined = notificationDecision {
+              self.needsNotificationDecision = true
+            } else {
+              self.needsNotificationDecision = false
+            }
+          }
+        }
+      }
+      .store(in: &cancellables)
+
   }
 
   func grantPermissionButtonTapped() {
@@ -62,6 +83,12 @@ public final class AskPermissionViewModel: ObservableObject {
     }
   }
 
+  #if os(iOS)
+    func grantNotificationButtonTapped() {
+      self.sessionNotificationHelper.askUserForNotificationPermissions()
+    }
+  #endif
+
   #if os(macOS)
     func closeAskPermissionWindow() {
       AppStore.WindowDefinition.askPermission.window()?.close()
@@ -101,6 +128,10 @@ public struct AskPermissionView: View {
             )
             .font(.body)
             .multilineTextAlignment(.center)
+            .padding(EdgeInsets(top: 0, leading: 5, bottom: 0, trailing: 5))
+            Spacer()
+            Image(systemName: "network.badge.shield.half.filled")
+              .imageScale(.large)
           #endif
           Spacer()
           Button("Grant VPN Permission") {
@@ -118,12 +149,36 @@ public struct AskPermissionView: View {
             .multilineTextAlignment(.center)
           #elseif os(iOS)
             Text(
-              "After tapping on the above button, tap on 'Allow' when prompted."
+              "After tapping the above button, tap 'Allow' when prompted."
+            )
+            .font(.caption)
+            .multilineTextAlignment(.center)
+          #endif
+        } else if $model.needsNotificationDecision.wrappedValue {
+          #if os(iOS)
+            Text(
+              "Firezone requires your permission to show local notifications when you need to sign in again."
+            )
+            .font(.body)
+            .multilineTextAlignment(.center)
+            .padding(EdgeInsets(top: 0, leading: 5, bottom: 0, trailing: 5))
+            Spacer()
+            Image(systemName: "bell")
+              .imageScale(.large)
+            Spacer()
+            Button("Grant Notification Permission") {
+              model.grantNotificationButtonTapped()
+            }
+            .buttonStyle(.borderedProminent)
+            .controlSize(.large)
+            Spacer()
+              .frame(maxHeight: 20)
+            Text(
+              "After tapping the above button, tap 'Allow' when prompted."
             )
             .font(.caption)
             .multilineTextAlignment(.center)
           #endif
-
         } else {
 
           #if os(macOS)
diff --git a/swift/apple/FirezoneKit/Sources/FirezoneKit/Features/WelcomeView.swift b/swift/apple/FirezoneKit/Sources/FirezoneKit/Features/WelcomeView.swift
index 874369922..e1f04efb1 100644
--- a/swift/apple/FirezoneKit/Sources/FirezoneKit/Features/WelcomeView.swift
+++ b/swift/apple/FirezoneKit/Sources/FirezoneKit/Features/WelcomeView.swift
@@ -40,6 +40,7 @@ import SwiftUINavigationCore
     }
 
     private let appStore: AppStore
+    private let sessionNotificationHelper: SessionNotificationHelper
 
     let settingsViewModel: SettingsViewModel
     @Published var isSettingsSheetPresented = false
@@ -48,32 +49,40 @@ import SwiftUINavigationCore
       self.appStore = appStore
       self.settingsViewModel = appStore.settingsViewModel
 
+      let sessionNotificationHelper = SessionNotificationHelper(logger: appStore.logger, authStore: appStore.authStore)
+      self.sessionNotificationHelper = sessionNotificationHelper
+
       appStore.objectWillChange
         .receive(on: mainQueue)
         .sink { [weak self] in self?.objectWillChange.send() }
         .store(in: &cancellables)
 
-      appStore.authStore.$loginStatus
-        .receive(on: mainQueue)
-        .sink(receiveValue: { [weak self] loginStatus in
-          guard let self else {
-            return
-          }
-
-          switch loginStatus {
-          case .signedIn:
-            self.state = .authenticated(MainViewModel(appStore: self.appStore))
-          case .signedOut:
-            self.state = .unauthenticated(AuthViewModel(authStore: self.appStore.authStore))
-          case .needsTunnelCreationPermission:
-            self.state = .needsPermission(
-              AskPermissionViewModel(tunnelStore: self.appStore.tunnelStore)
+      Publishers.CombineLatest(
+        appStore.authStore.$loginStatus,
+        sessionNotificationHelper.$notificationDecision
+      )
+      .receive(on: mainQueue)
+      .sink(receiveValue: { [weak self] loginStatus, notificationDecision in
+        guard let self else {
+          return
+        }
+        switch (loginStatus, notificationDecision) {
+        case (.uninitialized, _), (_, .uninitialized):
+          self.state = .uninitialized
+        case (.needsTunnelCreationPermission, _), (_, .notDetermined):
+          self.state = .needsPermission(
+            AskPermissionViewModel(
+              tunnelStore: self.appStore.tunnelStore,
+              sessionNotificationHelper: self.sessionNotificationHelper
             )
-          case .uninitialized:
-            self.state = .uninitialized
-          }
-        })
-        .store(in: &cancellables)
+          )
+        case (.signedOut, .determined):
+          self.state = .unauthenticated(AuthViewModel(authStore: self.appStore.authStore))
+        case (.signedIn, .determined):
+          self.state = .authenticated(MainViewModel(appStore: self.appStore))
+        }
+      })
+      .store(in: &cancellables)
     }
 
     func settingsButtonTapped() {
diff --git a/swift/apple/FirezoneKit/Sources/FirezoneKit/Helpers/SessionNotificationHelper.swift b/swift/apple/FirezoneKit/Sources/FirezoneKit/Helpers/SessionNotificationHelper.swift
new file mode 100644
index 000000000..b90bb8a71
--- /dev/null
+++ b/swift/apple/FirezoneKit/Sources/FirezoneKit/Helpers/SessionNotificationHelper.swift
@@ -0,0 +1,196 @@
+//
+//  SessionNotificationHelper.swift
+//  (c) 2024 Firezone, Inc.
+//  LICENSE: Apache-2.0
+//
+
+#if os(macOS)
+import AppKit
+#endif
+
+import Foundation
+
+#if os(iOS)
+import UserNotifications
+#endif
+
+
+// SessionNotificationHelper helps with showing iOS local notifications
+// when the session ends.
+// In macOS, it helps with showing an alert when the session ends.
+
+public enum NotificationIndentifier: String {
+  case sessionEndedNotificationCategory
+  case signInNotificationAction
+  case dismissNotificationAction
+}
+
+public class SessionNotificationHelper: NSObject {
+
+  enum NotificationDecision {
+    case uninitialized
+    case notDetermined
+    case determined(isNotificationAllowed: Bool)
+
+    var isInitialized: Bool {
+      switch self {
+      case .uninitialized: return false
+      default: return true
+      }
+    }
+  }
+
+  private let logger: AppLogger
+  private let authStore: AuthStore
+
+  @Published var notificationDecision: NotificationDecision = .uninitialized {
+    didSet {
+      self.logger.log(
+        "SessionNotificationHelper: notificationDecision changed to \(notificationDecision)"
+      )
+    }
+  }
+
+  public init(logger: AppLogger, authStore: AuthStore) {
+
+    self.logger = logger
+    self.authStore = authStore
+
+    super.init()
+
+    #if os(iOS)
+      let notificationCenter = UNUserNotificationCenter.current()
+    notificationCenter.delegate = self
+
+      let signInAction = UNNotificationAction(
+        identifier: NotificationIndentifier.signInNotificationAction.rawValue,
+        title: "Sign In",
+        options: [.authenticationRequired, .foreground])
+      let dismissAction = UNNotificationAction(
+        identifier: NotificationIndentifier.dismissNotificationAction.rawValue,
+        title: "Dismiss",
+        options: [])
+      let notificationActions = [signInAction, dismissAction]
+      let certificateExpiryCategory = UNNotificationCategory(
+        identifier: NotificationIndentifier.sessionEndedNotificationCategory.rawValue,
+        actions: notificationActions,
+        intentIdentifiers: [],
+        hiddenPreviewsBodyPlaceholder: "",
+        options: [])
+
+      notificationCenter.setNotificationCategories([certificateExpiryCategory])
+      notificationCenter.getNotificationSettings { notificationSettings in
+        self.logger.log(
+          "SessionNotificationHelper: getNotificationSettings returned. authorizationStatus is \(notificationSettings.authorizationStatus)"
+        )
+        switch notificationSettings.authorizationStatus {
+        case .notDetermined:
+          self.notificationDecision = .notDetermined
+        case .authorized:
+          self.notificationDecision = .determined(isNotificationAllowed: true)
+        case .denied:
+          self.notificationDecision = .determined(isNotificationAllowed: false)
+        default:
+          break
+        }
+      }
+    #endif
+  }
+
+  #if os(iOS)
+    func askUserForNotificationPermissions() {
+      guard case .notDetermined = self.notificationDecision else { return }
+      let notificationCenter = UNUserNotificationCenter.current()
+      notificationCenter.requestAuthorization(options: [.sound, .alert]) { isAuthorized, error in
+        self.logger.log(
+          "SessionNotificationHelper.askUserForNotificationPermissions: isAuthorized = \(isAuthorized)"
+        )
+        if let error = error {
+          self.logger.log(
+            "SessionNotificationHelper.askUserForNotificationPermissions: Error: \(error)"
+          )
+        }
+        self.notificationDecision = .determined(isNotificationAllowed: isAuthorized)
+      }
+    }
+  #endif
+
+  #if os(iOS)
+    // In iOS, use User Notifications.
+    // This gets called from the tunnel side.
+    public static func showSignedOutNotificationiOS(logger: AppLogger) {
+      UNUserNotificationCenter.current().getNotificationSettings { notificationSettings in
+        if notificationSettings.authorizationStatus == .authorized {
+          logger.log(
+            "Notifications are allowed. Alert style is \(notificationSettings.alertStyle.rawValue)"
+          )
+          let content = UNMutableNotificationContent()
+          content.title = "Your Firezone session has ended"
+          content.body = "Please sign in again to reconnect"
+          content.categoryIdentifier = NotificationIndentifier.sessionEndedNotificationCategory.rawValue
+          let trigger = UNTimeIntervalNotificationTrigger(timeInterval: 1, repeats: false)
+          let request = UNNotificationRequest(
+            identifier: "FirezoneTunnelShutdown", content: content, trigger: trigger
+          )
+          UNUserNotificationCenter.current().add(request) { error in
+            if let error = error {
+              logger.error("showSignedOutNotificationiOS: Error requesting notification: \(error)")
+            } else {
+              logger.error("showSignedOutNotificationiOS: Successfully requested notification")
+            }
+          }
+        }
+      }
+    }
+  #elseif os(macOS)
+    // In macOS, use a Cocoa alert.
+    // This gets called from the app side.
+    static func showSignedOutAlertmacOS(logger: AppLogger, authStore: AuthStore) {
+      let alert = NSAlert()
+      alert.messageText = "Your Firezone session has ended"
+      alert.informativeText = "Please sign in again to reconnect"
+      alert.addButton(withTitle: "Sign In")
+      alert.addButton(withTitle: "Cancel")
+      NSApp.activate(ignoringOtherApps: true)
+      let response = alert.runModal()
+      if response == NSApplication.ModalResponse.alertFirstButtonReturn {
+        logger.log("SessionNotificationHelper: \(#function): 'Sign In' clicked in notification")
+        Task {
+          do {
+            try await authStore.signIn()
+          } catch {
+            logger.error("Error signing in: \(error)")
+          }
+        }
+      }
+    }
+    #endif
+}
+
+#if os(iOS)
+  extension SessionNotificationHelper: UNUserNotificationCenterDelegate {
+    public func userNotificationCenter(_ center: UNUserNotificationCenter, didReceive response: UNNotificationResponse, withCompletionHandler completionHandler: @escaping () -> Void) {
+      self.logger.log("SessionNotificationHelper: \(#function): 'Sign In' clicked in notification")
+      let actionId = response.actionIdentifier
+      let categoryId = response.notification.request.content.categoryIdentifier
+      if categoryId == NotificationIndentifier.sessionEndedNotificationCategory.rawValue,
+         actionId == NotificationIndentifier.signInNotificationAction.rawValue {
+        // User clicked on 'Sign In' in the notification
+        Task {
+          do {
+            try await self.authStore.signIn()
+          } catch {
+            self.logger.error("Error signing in: \(error)")
+          }
+          DispatchQueue.main.async {
+            completionHandler()
+          }
+        }
+      } else {
+        DispatchQueue.main.async {
+          completionHandler()
+        }
+      }
+    }
+  }
+#endif
diff --git a/swift/apple/FirezoneKit/Sources/FirezoneKit/Helpers/TunnelShutdownEvent.swift b/swift/apple/FirezoneKit/Sources/FirezoneKit/Helpers/TunnelShutdownEvent.swift
index ff83c981a..0d33a089f 100644
--- a/swift/apple/FirezoneKit/Sources/FirezoneKit/Helpers/TunnelShutdownEvent.swift
+++ b/swift/apple/FirezoneKit/Sources/FirezoneKit/Helpers/TunnelShutdownEvent.swift
@@ -34,11 +34,30 @@ public struct TunnelShutdownEvent: Codable, CustomStringConvertible {
       case .invalidAdapterState: return "invalid adapter state"
       }
     }
+
+    public var action: Action {
+      switch self {
+      case .stopped(let reason):
+        if reason == .userInitiated {
+          return .signoutImmediatelySilently
+        } else if reason == .userLogout || reason == .userSwitch {
+          return .doNothing
+        } else {
+          return .retryThenSignout
+        }
+      case .networkSettingsApplyFailure, .invalidAdapterState:
+        return .retryThenSignout
+      case .connlibConnectFailure, .connlibDisconnected,
+        .badTunnelConfiguration, .tokenNotFound:
+        return .signoutImmediately
+      }
+    }
   }
 
   public enum Action {
     case doNothing
     case signoutImmediately
+    case signoutImmediatelySilently
     case retryThenSignout
   }
 
@@ -46,23 +65,7 @@ public struct TunnelShutdownEvent: Codable, CustomStringConvertible {
   public let errorMessage: String
   public let date: Date
 
-  public var action: Action {
-    switch reason {
-    case .stopped(let reason):
-      if reason == .userInitiated {
-        return .signoutImmediately
-      } else if reason == .userLogout || reason == .userSwitch {
-        return .doNothing
-      } else {
-        return .retryThenSignout
-      }
-    case .networkSettingsApplyFailure, .invalidAdapterState:
-      return .retryThenSignout
-    case .connlibConnectFailure, .connlibDisconnected,
-      .badTunnelConfiguration, .tokenNotFound:
-      return .signoutImmediately
-    }
-  }
+  public var action: Action { reason.action }
 
   public var description: String {
     "(\(reason)\(action == .signoutImmediately ? " (needs immediate signout)" : ""), error: '\(errorMessage)', date: \(date))"
diff --git a/swift/apple/FirezoneKit/Sources/FirezoneKit/Stores/AppStore.swift b/swift/apple/FirezoneKit/Sources/FirezoneKit/Stores/AppStore.swift
index 523da12cd..d393c3819 100644
--- a/swift/apple/FirezoneKit/Sources/FirezoneKit/Stores/AppStore.swift
+++ b/swift/apple/FirezoneKit/Sources/FirezoneKit/Stores/AppStore.swift
@@ -66,7 +66,7 @@ public final class AppStore: ObservableObject {
   public let settingsViewModel: SettingsViewModel
 
   private var cancellables: Set<AnyCancellable> = []
-  let logger: AppLogger
+  public let logger: AppLogger
 
   public init() {
     let logger = AppLogger(process: .app, folderURL: SharedAccess.appLogFolderURL)
diff --git a/swift/apple/FirezoneKit/Sources/FirezoneKit/Stores/AuthStore.swift b/swift/apple/FirezoneKit/Sources/FirezoneKit/Stores/AuthStore.swift
index 358e2360b..2b017a8e5 100644
--- a/swift/apple/FirezoneKit/Sources/FirezoneKit/Stores/AuthStore.swift
+++ b/swift/apple/FirezoneKit/Sources/FirezoneKit/Stores/AuthStore.swift
@@ -10,6 +10,10 @@ import Foundation
 import NetworkExtension
 import OSLog
 
+#if os(macOS)
+  import AppKit
+#endif
+
 @MainActor
 public final class AuthStore: ObservableObject {
   enum LoginStatus: CustomStringConvertible {
@@ -202,6 +206,13 @@ public final class AuthStore: ObservableObject {
         Task {
           await self.signOut()
         }
+        #if os(macOS)
+          SessionNotificationHelper.showSignedOutAlertmacOS(logger: self.logger, authStore: self)
+        #endif
+      case .signoutImmediatelySilently:
+        Task {
+          await self.signOut()
+        }
       case .retryThenSignout:
         self.retryStartTunnel()
       case .doNothing:
@@ -230,6 +241,9 @@ public final class AuthStore: ObservableObject {
       Task {
         await self.signOut()
       }
+      #if os(macOS)
+        SessionNotificationHelper.showSignedOutAlertmacOS(logger: self.logger, authStore: self)
+      #endif
     }
   }
 
diff --git a/swift/apple/FirezoneNetworkExtension/PacketTunnelProvider.swift b/swift/apple/FirezoneNetworkExtension/PacketTunnelProvider.swift
index 0964a1b2b..5cc8156e7 100644
--- a/swift/apple/FirezoneNetworkExtension/PacketTunnelProvider.swift
+++ b/swift/apple/FirezoneNetworkExtension/PacketTunnelProvider.swift
@@ -109,6 +109,12 @@ class PacketTunnelProvider: NEPacketTunnelProvider {
 
   func handleTunnelShutdown(dueTo reason: TunnelShutdownEvent.Reason, errorMessage: String) {
     TunnelShutdownEvent.saveToDisk(reason: reason, errorMessage: errorMessage, logger: self.logger)
+
+    #if os(iOS)
+      if reason.action == .signoutImmediately {
+        SessionNotificationHelper.showSignedOutNotificationiOS(logger: self.logger)
+      }
+    #endif
   }
 }