android: stop tailscaled when VPN has been revoked (#480)

-add new Ipn UI state 'Stopping' to handle the case where the VPN is no longer active and a request to stop Tailscale has been issued (but is not complete yet) and use for optimistic UI
-when VPN has been revoked, stop tailscaled and set the state to Stopping
-this fixes the race condition where when we tell tailscaled to stop, stopping races against the netmap state updating as a result of the VPN being revoked
-add isActive state and use instead of isPrepared for UI showing whether we are connected - we were previously using isPrepared as a proxy for connection, but sometimes the VPN has been prepared but is not active (eg when VPN permissions have been given and VPN has been connected previously, but has been revoked)
-refactor network callbacks into its own class for readability

Fixes tailscale/tailscale#12850

Signed-off-by: kari-ts <kari@tailscale.com>

android/src/main/java/com/tailscale/ipn/App.kt

@@ -12,10 +12,6 @@ import android.content.Intent
 import android.content.SharedPreferences
 import android.content.pm.PackageManager
 import android.net.ConnectivityManager
-import android.net.LinkProperties
-import android.net.Network
-import android.net.NetworkCapabilities
-import android.net.NetworkRequest
 import android.os.Build
 import android.os.Environment
 import android.util.Log
@@ -45,7 +41,6 @@ import kotlinx.serialization.json.Json
 import libtailscale.Libtailscale
 import java.io.File
 import java.io.IOException
-import java.net.InetAddress
 import java.net.NetworkInterface
 import java.security.GeneralSecurityException
 import java.util.Locale
@@ -56,11 +51,6 @@ class App : UninitializedApp(), libtailscale.AppContext, ViewModelStoreOwner {
   companion object {
     private const val FILE_CHANNEL_ID = "tailscale-files"
     private const val TAG = "App"
-    private val networkConnectivityRequest =
-        NetworkRequest.Builder()
-            .addCapability(NetworkCapabilities.NET_CAPABILITY_INTERNET)
-            .addCapability(NetworkCapabilities.NET_CAPABILITY_NOT_VPN)
-            .build()
     private lateinit var appInstance: App
 
     /**
@@ -81,9 +71,6 @@ class App : UninitializedApp(), libtailscale.AppContext, ViewModelStoreOwner {
   override val viewModelStore: ViewModelStore
     get() = appViewModelStore
 
-  lateinit var vpnViewModel: VpnViewModel
-    private set
-
   private val appViewModelStore: ViewModelStore by lazy { ViewModelStore() }
 
   var healthNotifier: HealthNotifier? = null
@@ -147,7 +134,8 @@ class App : UninitializedApp(), libtailscale.AppContext, ViewModelStoreOwner {
     Notifier.start(applicationScope)
     healthNotifier = HealthNotifier(Notifier.health, applicationScope)
     connectivityManager = this.getSystemService(Context.CONNECTIVITY_SERVICE) as ConnectivityManager
-    setAndRegisterNetworkCallbacks()
+    NetworkChangeCallback.monitorDnsChanges(connectivityManager, dns)
+    initViewModels()
     applicationScope.launch {
       Notifier.state.collect { state ->
         val ableToStartVPN = state > Ipn.State.NeedsMachineAuth
@@ -161,14 +149,13 @@ class App : UninitializedApp(), libtailscale.AppContext, ViewModelStoreOwner {
         QuickToggleService.setVPNRunning(vpnRunning)
       }
     }
-    initViewModels()
   }
 
   private fun initViewModels() {
     vpnViewModel = ViewModelProvider(this, VpnViewModelFactory(this)).get(VpnViewModel::class.java)
   }
 
-  fun setWantRunning(wantRunning: Boolean) {
+  fun setWantRunning(wantRunning: Boolean, onSuccess: (() -> Unit)? = null) {
     val callback: (Result<Ipn.Prefs>) -> Unit = { result ->
       result.fold(
           onSuccess = {},
@@ -180,41 +167,6 @@ class App : UninitializedApp(), libtailscale.AppContext, ViewModelStoreOwner {
         .editPrefs(Ipn.MaskedPrefs().apply { WantRunning = wantRunning }, callback)
   }
 
-  // requestNetwork attempts to find the best network that matches the passed NetworkRequest. It is
-  // possible that this might return an unusuable network, eg a captive portal.
-  private fun setAndRegisterNetworkCallbacks() {
-    connectivityManager.requestNetwork(
-        networkConnectivityRequest,
-        object : ConnectivityManager.NetworkCallback() {
-          override fun onAvailable(network: Network) {
-            super.onAvailable(network)
-
-            val sb = StringBuilder()
-            val linkProperties: LinkProperties? = connectivityManager.getLinkProperties(network)
-            val dnsList: MutableList<InetAddress> = linkProperties?.dnsServers ?: mutableListOf()
-            for (ip in dnsList) {
-              sb.append(ip.hostAddress).append(" ")
-            }
-            val searchDomains: String? = linkProperties?.domains
-            if (searchDomains != null) {
-              sb.append("\n")
-              sb.append(searchDomains)
-            }
-
-            if (dns.updateDNSFromNetwork(sb.toString())) {
-              Libtailscale.onDNSConfigChanged(linkProperties?.interfaceName)
-            }
-          }
-
-          override fun onLost(network: Network) {
-            super.onLost(network)
-            if (dns.updateDNSFromNetwork("")) {
-              Libtailscale.onDNSConfigChanged("")
-            }
-          }
-        })
-  }
-
   // encryptToPref a byte array of data using the Jetpack Security
   // library and writes it to a global encrypted preference store.
   @Throws(IOException::class, GeneralSecurityException::class)
@@ -389,6 +341,8 @@ open class UninitializedApp : Application() {
     private lateinit var appInstance: UninitializedApp
     lateinit var notificationManager: NotificationManagerCompat
 
+    lateinit var vpnViewModel: VpnViewModel
+
     @JvmStatic
     fun get(): UninitializedApp {
       return appInstance
@@ -550,6 +504,10 @@ open class UninitializedApp : Application() {
     return builtInDisallowedPackageNames + userDisallowed
   }
 
+  fun getAppScopedViewModel(): VpnViewModel {
+    return vpnViewModel
+  }
+
   val builtInDisallowedPackageNames: List<String> =
       listOf(
           // RCS/Jibe https://github.com/tailscale/tailscale/issues/2322

android/src/main/java/com/tailscale/ipn/IPNService.kt

@@ -10,33 +10,40 @@ import android.os.Build
 import android.system.OsConstants
 import android.util.Log
 import com.tailscale.ipn.mdm.MDMSettings
+import com.tailscale.ipn.ui.model.Ipn
+import com.tailscale.ipn.ui.notifier.Notifier
 import libtailscale.Libtailscale
 import java.util.UUID
 
 open class IPNService : VpnService(), libtailscale.IPNService {
   private val TAG = "IPNService"
   private val randomID: String = UUID.randomUUID().toString()
+  private lateinit var app: App
 
   override fun id(): String {
     return randomID
   }
 
+  override fun updateVpnStatus(status: Boolean) {
+    app.getAppScopedViewModel().setVpnActive(status)
+  }
+
   override fun onCreate() {
     super.onCreate()
     // grab app to make sure it initializes
-    App.get()
+    app = App.get()
   }
 
   override fun onStartCommand(intent: Intent?, flags: Int, startId: Int): Int =
       when (intent?.action) {
         ACTION_STOP_VPN -> {
-          App.get().setWantRunning(false)
+          app.setWantRunning(false)
           close()
           START_NOT_STICKY
         }
         ACTION_START_VPN -> {
           showForegroundNotification()
-          App.get().setWantRunning(true)
+          app.setWantRunning(true)
           Libtailscale.requestVPN(this)
           START_STICKY
         }
@@ -44,8 +51,8 @@ open class IPNService : VpnService(), libtailscale.IPNService {
           // This means we were started by Android due to Always On VPN.
           // We show a non-foreground notification because we weren't
           // started as a foreground service.
-          App.get().notifyStatus(true)
-          App.get().setWantRunning(true)
+          app.notifyStatus(true)
+          app.setWantRunning(true)
           Libtailscale.requestVPN(this)
           START_STICKY
         }
@@ -64,6 +71,8 @@ open class IPNService : VpnService(), libtailscale.IPNService {
       }
 
   override fun close() {
+    app.setWantRunning(false) { updateVpnStatus(false) }
+    Notifier.setState(Ipn.State.Stopping)
     stopForeground(STOP_FOREGROUND_REMOVE)
     Libtailscale.serviceDisconnect(this)
   }
@@ -78,6 +87,10 @@ open class IPNService : VpnService(), libtailscale.IPNService {
     super.onRevoke()
   }
 
+  private fun setVpnPrepared(isPrepared: Boolean) {
+    app.getAppScopedViewModel().setVpnPrepared(isPrepared)
+  }
+
   private fun showForegroundNotification() {
     try {
       startForeground(

android/src/main/java/com/tailscale/ipn/MainActivity.kt

@@ -89,7 +89,7 @@ class MainActivity : ComponentActivity() {
   private lateinit var vpnPermissionLauncher: ActivityResultLauncher<Intent>
   private val viewModel: MainViewModel by lazy {
     val app = App.get()
-    vpnViewModel = app.vpnViewModel
+    vpnViewModel = app.getAppScopedViewModel()
     ViewModelProvider(this, MainViewModelFactory(vpnViewModel)).get(MainViewModel::class.java)
   }
   private lateinit var vpnViewModel: VpnViewModel
@@ -137,7 +137,7 @@ class MainActivity : ComponentActivity() {
               showOtherVPNConflictDialog()
             } else {
               Log.d("VpnPermission", "Permission was denied by the user")
-              viewModel.setVpnPrepared(false)
+              vpnViewModel.setVpnPrepared(false)
             }
           }
         }

android/src/main/java/com/tailscale/ipn/NetworkChangeCallback.kt

@@ -0,0 +1,58 @@
+// Copyright (c) Tailscale Inc & AUTHORS
+// SPDX-License-Identifier: BSD-3-Clause
+package com.tailscale.ipn
+
+import android.content.Context
+import android.net.ConnectivityManager
+import android.net.LinkProperties
+import android.net.Network
+import android.net.NetworkCapabilities
+import android.net.NetworkRequest
+import android.util.Log
+import libtailscale.Libtailscale
+import java.net.InetAddress
+import java.net.NetworkInterface
+
+object NetworkChangeCallback {
+
+  // requestNetwork attempts to find the best network that matches the passed NetworkRequest. It is
+  // possible that this might return an unusuable network, eg a captive portal.
+  fun monitorDnsChanges(connectivityManager: ConnectivityManager, dns: DnsConfig) {
+    val networkConnectivityRequest =
+        NetworkRequest.Builder()
+            .addCapability(NetworkCapabilities.NET_CAPABILITY_INTERNET)
+            .addCapability(NetworkCapabilities.NET_CAPABILITY_NOT_VPN)
+            .build()
+
+    connectivityManager.registerNetworkCallback(
+        networkConnectivityRequest,
+        object : ConnectivityManager.NetworkCallback() {
+          override fun onAvailable(network: Network) {
+            super.onAvailable(network)
+
+            val sb = StringBuilder()
+            val linkProperties: LinkProperties? = connectivityManager.getLinkProperties(network)
+            val dnsList: MutableList<InetAddress> = linkProperties?.dnsServers ?: mutableListOf()
+            for (ip in dnsList) {
+              sb.append(ip.hostAddress).append(" ")
+            }
+            val searchDomains: String? = linkProperties?.domains
+            if (searchDomains != null) {
+              sb.append("\n")
+              sb.append(searchDomains)
+            }
+
+            if (dns.updateDNSFromNetwork(sb.toString())) {
+              Libtailscale.onDNSConfigChanged(linkProperties?.interfaceName)
+            }
+          }
+
+          override fun onLost(network: Network) {
+            super.onLost(network)
+            if (dns.updateDNSFromNetwork("")) {
+              Libtailscale.onDNSConfigChanged("")
+            }
+          }
+        })
+  }
+}

android/src/main/java/com/tailscale/ipn/ui/model/Ipn.kt

@@ -18,7 +18,11 @@ class Ipn {
     NeedsMachineAuth(3),
     Stopped(4),
     Starting(5),
-    Running(6);
+    Running(6),
+    // Stopping represents a state where a request to stop Tailscale has been issue but has not
+    // completed. This state allows UI to optimistically reflect a stopped state, and to fallback if
+    // necessary.
+    Stopping(7);
 
     companion object {
       fun fromInt(value: Int): State {

android/src/main/java/com/tailscale/ipn/ui/notifier/Notifier.kt

@@ -33,7 +33,8 @@ object Notifier {
   private val decoder = Json { ignoreUnknownKeys = true }
 
   // General IPN Bus State
-  val state: StateFlow<Ipn.State> = MutableStateFlow(Ipn.State.NoState)
+  private val _state = MutableStateFlow(Ipn.State.NoState)
+  val state: StateFlow<Ipn.State> = _state
   val netmap: StateFlow<Netmap.NetworkMap?> = MutableStateFlow(null)
   val prefs: StateFlow<Ipn.Prefs?> = MutableStateFlow(null)
   val engineStatus: StateFlow<Ipn.EngineStatus?> = MutableStateFlow(null)
@@ -107,4 +108,8 @@ object Notifier {
     InitialOutgoingFiles(64),
     InitialHealthState(128),
   }
+
+  fun setState(newState: Ipn.State) {
+    _state.value = newState
+}
 }

android/src/main/java/com/tailscale/ipn/ui/view/MainView.kt

@@ -232,6 +232,9 @@ fun MainView(
                 ConnectView(
                     state,
                     isPrepared,
+                    // If Tailscale is stopping, don't automatically restart; wait for user to take
+                    // action (eg, if the user connected to another VPN).
+                    state != Ipn.State.Stopping,
                     user,
                     { viewModel.toggleVpn() },
                     { viewModel.login() },
@@ -407,6 +410,7 @@ fun StartingView() {
 fun ConnectView(
     state: Ipn.State,
     isPrepared: Boolean,
+    shouldStartAutomatically: Boolean,
     user: IpnLocal.LoginProfile?,
     connectAction: () -> Unit,
     loginAction: () -> Unit,
@@ -415,7 +419,7 @@ fun ConnectView(
     showVPNPermissionLauncherIfUnauthorized: () -> Unit
 ) {
   LaunchedEffect(isPrepared) {
-    if (!isPrepared) {
+    if (!isPrepared && shouldStartAutomatically) {
       showVPNPermissionLauncherIfUnauthorized()
     }
   }

android/src/main/java/com/tailscale/ipn/ui/viewModel/IpnViewModel.kt

@@ -134,11 +134,6 @@ open class IpnViewModel : ViewModel() {
   }
 
   // VPN Control
-
-  fun setVpnPrepared(prepared: Boolean) {
-    _vpnPrepared.value = prepared
-  }
-
   fun startVPN() {
     UninitializedApp.get().startVPN()
   }

android/src/main/java/com/tailscale/ipn/ui/viewModel/MainViewModel.kt

@@ -72,6 +72,8 @@ class MainViewModel(private val vpnViewModel: VpnViewModel) : IpnViewModel() {
 
   val isVpnPrepared: StateFlow<Boolean> = vpnViewModel.vpnPrepared
 
+  val isVpnActive: StateFlow<Boolean> = vpnViewModel.vpnActive
+
   // Icon displayed in the button to present the health view
   val healthIcon: StateFlow<Int?> = MutableStateFlow(null)
 
@@ -97,28 +99,30 @@ class MainViewModel(private val vpnViewModel: VpnViewModel) : IpnViewModel() {
     viewModelScope.launch {
       var previousState: State? = null
 
-      combine(Notifier.state, isVpnPrepared) { state, prepared -> state to prepared }
-          .collect { (currentState, prepared) ->
-            stateRes.set(userStringRes(currentState, previousState, prepared))
+      combine(Notifier.state, isVpnActive) { state, active -> state to active }
+          .collect { (currentState, active) ->
+            // Determine the correct state resource string
+            stateRes.set(userStringRes(currentState, previousState, active))
 
+            // Determine if the VPN toggle should be on
             val isOn =
                 when {
-                  prepared && currentState == State.Running || currentState == State.Starting ->
-                      true
-                  previousState == State.NoState && currentState == State.Starting ->
+                  active && (currentState == State.Running || currentState == State.Starting) ->
                       true
+                  previousState == State.NoState && currentState == State.Starting -> true
                   else -> false
                 }
 
+            // Update the VPN toggle state
             _vpnToggleState.value = isOn
+
+            // Update the previous state
             previousState = currentState
           }
     }
 
     viewModelScope.launch {
-      searchTerm
-        .debounce(250L)
-        .collect { term ->
+      searchTerm.debounce(250L).collect { term ->
         peers.set(peerCategorizer.groupedAndFilteredPeers(term))
       }
     }
@@ -181,17 +185,17 @@ class MainViewModel(private val vpnViewModel: VpnViewModel) : IpnViewModel() {
   }
 }
 
-private fun userStringRes(currentState: State?, previousState: State?, vpnPrepared: Boolean): Int {
+private fun userStringRes(currentState: State?, previousState: State?, vpnActive: Boolean): Int {
   return when {
     previousState == State.NoState && currentState == State.Starting -> R.string.starting
     currentState == State.NoState -> R.string.placeholder
     currentState == State.InUseOtherUser -> R.string.placeholder
     currentState == State.NeedsLogin ->
-        if (vpnPrepared) R.string.please_login else R.string.connect_to_vpn
+        if (vpnActive) R.string.please_login else R.string.connect_to_vpn
     currentState == State.NeedsMachineAuth -> R.string.needs_machine_auth
     currentState == State.Stopped -> R.string.stopped
     currentState == State.Starting -> R.string.starting
-    currentState == State.Running -> if (vpnPrepared) R.string.connected else R.string.placeholder
+    currentState == State.Running -> if (vpnActive) R.string.connected else R.string.placeholder
     else -> R.string.placeholder
   }
 }

android/src/main/java/com/tailscale/ipn/ui/viewModel/VpnViewModel.kt

@@ -26,9 +26,12 @@ class VpnViewModelFactory(private val application: Application) : ViewModelProvi
 // application scoped because Tailscale might be toggled on and off outside of the activity
 // lifecycle.
 class VpnViewModel(application: Application) : AndroidViewModel(application) {
-  // Whether the VPN is prepared
+  // Whether the VPN is prepared. This is set to true if the VPN application is already prepared, or if the user has previously consented to the VPN application. This is used to determine whether a VPN permission launcher needs to be shown. 
   val _vpnPrepared = MutableStateFlow(false)
   val vpnPrepared: StateFlow<Boolean> = _vpnPrepared
+  // Whether a VPN interface has been established. This is set by net.updateTUN upon VpnServiceBuilder.establish, and consumed by UI to reflect VPN state. 
+  val _vpnActive = MutableStateFlow(false)
+  val vpnActive: StateFlow<Boolean> = _vpnActive
   val TAG = "VpnViewModel"
 
   init {
@@ -49,7 +52,11 @@ class VpnViewModel(application: Application) : AndroidViewModel(application) {
     }
   }
 
-  fun setVpnPrepared(prepared: Boolean) {
-    _vpnPrepared.value = prepared
+  fun setVpnActive(isActive: Boolean) {
+    _vpnActive.value = isActive
+  }
+
+  fun setVpnPrepared(isPrepared: Boolean) {
+    _vpnPrepared.value = isPrepared
   }
 }

go.mod

@@ -5,7 +5,6 @@ go 1.22.0
 require (
 	github.com/tailscale/wireguard-go v0.0.0-20240731203015-71393c576b98
 	golang.org/x/mobile v0.0.0-20240319015410-c58ccf4b0c87
-	golang.org/x/sys v0.22.0
 	inet.af/netaddr v0.0.0-20220617031823-097006376321
 	tailscale.com v1.73.0-pre.0.20240821174438-af3d3c433b67
 )
@@ -87,6 +86,7 @@ require (
 	golang.org/x/mod v0.19.0 // indirect
 	golang.org/x/net v0.27.0 // indirect
 	golang.org/x/sync v0.7.0 // indirect
+	golang.org/x/sys v0.22.0 // indirect
 	golang.org/x/term v0.22.0 // indirect
 	golang.org/x/text v0.16.0 // indirect
 	golang.org/x/time v0.5.0 // indirect

libtailscale/backend.go

@@ -150,7 +150,6 @@ func (a *App) runBackend(ctx context.Context) error {
 		cfg        configPair
 		state      ipn.State
 		networkMap *netmap.NetworkMap
-		service    IPNService
 	)
 
 	stateCh := make(chan ipn.State)
@@ -168,9 +167,9 @@ func (a *App) runBackend(ctx context.Context) error {
 		select {
 		case s := <-stateCh:
 			state = s
-			if cfg.rcfg != nil && state >= ipn.Starting && service != nil {
+			if cfg.rcfg != nil && state >= ipn.Starting && vpnService.service != nil {
 				// On state change, check if there are router or config changes requiring an update to VPNBuilder
-				if err := b.updateTUN(service, cfg.rcfg, cfg.dcfg); err != nil {
+				if err := b.updateTUN(vpnService.service, cfg.rcfg, cfg.dcfg); err != nil {
 					if errors.Is(err, errMultipleUsers) {
 						// TODO: surface error to user
 					}
@@ -193,13 +192,13 @@ func (a *App) runBackend(ctx context.Context) error {
 			networkMap = n
 		case c := <-configs:
 			cfg = c
-			if b == nil || service == nil || cfg.rcfg == nil {
+			if b == nil || vpnService.service == nil || cfg.rcfg == nil {
 				configErrs <- nil
 				break
 			}
-			configErrs <- b.updateTUN(service, cfg.rcfg, cfg.dcfg)
+			configErrs <- b.updateTUN(vpnService.service, cfg.rcfg, cfg.dcfg)
 		case s := <-onVPNRequested:
-			if service != nil && service.ID() == s.ID() {
+			if vpnService.service != nil && vpnService.service.ID() == s.ID() {
 				// Still the same VPN instance, do nothing
 				break
 			}
@@ -228,24 +227,24 @@ func (a *App) runBackend(ctx context.Context) error {
 			// See https://github.com/tailscale/corp/issues/13814
 			b.backend.DebugRebind()
 
-			service = s
+			vpnService.service = s
 
 			if networkMap != nil {
 				// TODO
 			}
 			if cfg.rcfg != nil && state >= ipn.Starting {
-				if err := b.updateTUN(service, cfg.rcfg, cfg.dcfg); err != nil {
+				if err := b.updateTUN(vpnService.service, cfg.rcfg, cfg.dcfg); err != nil {
 					log.Printf("VPN update failed: %v", err)
-					service.Close()
+					vpnService.service.Close()
 					b.lastCfg = nil
 					b.CloseTUNs()
 				}
 			}
 		case s := <-onDisconnect:
 			b.CloseTUNs()
-			if service != nil && service.ID() == s.ID() {
+			if vpnService.service != nil && vpnService.service.ID() == s.ID() {
 				netns.SetAndroidProtectFunc(nil)
-				service = nil
+				vpnService.service = nil
 			}
 		case i := <-onDNSConfigChanged:
 			if b != nil {

libtailscale/interfaces.go

@@ -3,7 +3,9 @@
 
 package libtailscale
 
-import _ "golang.org/x/mobile/bind"
+import (
+	_ "golang.org/x/mobile/bind"
+)
 
 // Start starts the application, storing state in the given dataDir and using
 // the given appCtx.
@@ -73,6 +75,8 @@ type IPNService interface {
 	NewBuilder() VPNServiceBuilder
 
 	Close()
+
+	UpdateVpnStatus(bool)
 }
 
 // VPNServiceBuilder corresponds to Android's VpnService.Builder.

libtailscale/net.go

@@ -12,9 +12,9 @@ import (
 	"reflect"
 	"runtime/debug"
 	"strings"
+	"syscall"
 
 	"github.com/tailscale/wireguard-go/tun"
-	"golang.org/x/sys/unix"
 	"inet.af/netaddr"
 	"tailscale.com/net/dns"
 	"tailscale.com/net/netmon"
@@ -33,6 +33,15 @@ var errVPNNotPrepared = errors.New("VPN service not prepared or was revoked")
 //	https://github.com/tailscale/tailscale/issues/2180
 var errMultipleUsers = errors.New("VPN cannot be created on this device due to an Android bug with multiple users")
 
+// VpnService contains the IPNService class from Android, the file descriptor, and whether the descriptor has been detached.
+type VpnService struct {
+	service    IPNService
+	fd         int32
+	fdDetached bool
+}
+
+var vpnService = &VpnService{}
+
 // Report interfaces in the device in net.Interface format.
 func (a *App) getInterfaces() ([]netmon.Interface, error) {
 	var ifaces []netmon.Interface
@@ -138,7 +147,8 @@ func (b *backend) updateTUN(service IPNService, rcfg *router.Config, dcfg *dns.O
 	if len(rcfg.LocalAddrs) == 0 {
 		return nil
 	}
-	builder := service.NewBuilder()
+	vpnService.service = service
+	builder := vpnService.service.NewBuilder()
 	b.logger.Logf("updateTUN: got new builder")
 
 	if err := builder.SetMTU(defaultMTU); err != nil {
@@ -193,10 +203,15 @@ func (b *backend) updateTUN(service IPNService, rcfg *router.Config, dcfg *dns.O
 	parcelFD, err := builder.Establish()
 	if err != nil {
 		if strings.Contains(err.Error(), "INTERACT_ACROSS_USERS") {
+			// Update VPN status if VPN interface cannot be created
+			b.logger.Logf("updateTUN: could not establish VPN because %v", err)
+			vpnService.service.UpdateVpnStatus(false)
 			return errMultipleUsers
 		}
 		return fmt.Errorf("VpnService.Builder.establish: %v", err)
 	}
+	log.Printf("Setting vpn activity status to true")
+	vpnService.service.UpdateVpnStatus(true)
 	b.logger.Logf("updateTUN: established VPN")
 
 	if parcelFD == nil {
@@ -205,6 +220,9 @@ func (b *backend) updateTUN(service IPNService, rcfg *router.Config, dcfg *dns.O
 
 	// detachFd.
 	tunFD, err := parcelFD.Detach()
+	vpnService.fdDetached = true
+	vpnService.fd = tunFD
+
 	if err != nil {
 		return fmt.Errorf("detachFd: %v", err)
 	}
@@ -213,7 +231,7 @@ func (b *backend) updateTUN(service IPNService, rcfg *router.Config, dcfg *dns.O
 	// Create TUN device.
 	tunDev, _, err := tun.CreateUnmonitoredTUNFromFD(int(tunFD))
 	if err != nil {
-		unix.Close(int(tunFD))
+		closeFileDescriptor()
 		return err
 	}
 	b.logger.Logf("updateTUN: created TUN device")
@@ -226,10 +244,21 @@ func (b *backend) updateTUN(service IPNService, rcfg *router.Config, dcfg *dns.O
 	return nil
 }
 
+func closeFileDescriptor() error {
+	if vpnService.fd != -1 && vpnService.fdDetached {
+		err := syscall.Close(int(vpnService.fd))
+		vpnService.fd = -1
+		vpnService.fdDetached = false
+		return fmt.Errorf("error closing file descriptor: %w", err)
+	}
+	return nil
+}
+
 // CloseVPN closes any active TUN devices.
 func (b *backend) CloseTUNs() {
 	b.lastCfg = nil
 	b.devices.Shutdown()
+	vpnService.service = nil
 }
 
 // ifname is the interface name retrieved from LinkProperties on network change. If a network is lost, an empty string is passed in.