diff --git a/app/phone/src/main/java/com/nomadics9/ananas/MainActivity.kt b/app/phone/src/main/java/com/nomadics9/ananas/MainActivity.kt
index 74a3c1a5..9ab4735b 100644
--- a/app/phone/src/main/java/com/nomadics9/ananas/MainActivity.kt
+++ b/app/phone/src/main/java/com/nomadics9/ananas/MainActivity.kt
@@ -4,6 +4,7 @@ import android.os.Bundle
 import android.view.View
 import androidx.activity.viewModels
 import androidx.appcompat.app.AppCompatActivity
+import androidx.lifecycle.lifecycleScope
 import androidx.navigation.NavController
 import androidx.navigation.NavGraph
 import androidx.navigation.fragment.NavHostFragment
@@ -22,6 +23,10 @@ import com.nomadics9.ananas.database.ServerDatabaseDao
 import com.nomadics9.ananas.databinding.ActivityMainBinding
 import com.nomadics9.ananas.viewmodels.MainViewModel
 import com.nomadics9.ananas.work.SyncWorker
+import com.nomadics9.ananas.repository.JellyfinRepository
+import com.nomadics9.ananas.utils.restart
+import kotlinx.coroutines.delay
+import kotlinx.coroutines.launch
 import javax.inject.Inject
 import com.nomadics9.ananas.core.R as CoreR
 
@@ -35,6 +40,9 @@ class MainActivity : AppCompatActivity() {
     @Inject
     lateinit var database: ServerDatabaseDao
 
+    @Inject
+    lateinit var jellyfinRepository: JellyfinRepository
+
     @Inject
     lateinit var appPreferences: AppPreferences
 
@@ -68,10 +76,18 @@ class MainActivity : AppCompatActivity() {
         val navView: NavigationBarView = binding.navView as NavigationBarView
 
         if (appPreferences.offlineMode) {
+            appPreferences.isOffline = true
+        }
+
+        if (appPreferences.isOffline) {
             navView.menu.clear()
             navView.inflateMenu(CoreR.menu.bottom_nav_menu_offline)
         }
 
+        if (!appPreferences.isOffline && appPreferences.autoOffline) {
+            testServerConnection()
+        }
+
         setSupportActionBar(binding.mainToolbar)
 
         // Passing each menu ID as a set of Ids because each
@@ -152,4 +168,18 @@ class MainActivity : AppCompatActivity() {
             setTheme(CoreR.style.ThemeOverlay_Findroid_Amoled)
         }
     }
+
+    private fun testServerConnection() {
+        val activity = this
+        lifecycleScope.launch {
+            try {
+                jellyfinRepository.getPublicSystemInfo()
+                // Give the UI a chance to load
+                delay(100)
+            } catch (e: Exception) {
+                appPreferences.isOffline = true
+                activity.restart()
+            }
+        }
+    }
 }
diff --git a/core/src/main/java/com/nomadics9/ananas/di/RepositoryModule.kt b/core/src/main/java/com/nomadics9/ananas/di/RepositoryModule.kt
index a0a818fc..b3f7a9a8 100644
--- a/core/src/main/java/com/nomadics9/ananas/di/RepositoryModule.kt
+++ b/core/src/main/java/com/nomadics9/ananas/di/RepositoryModule.kt
@@ -48,7 +48,7 @@ object RepositoryModule {
         appPreferences: AppPreferences,
     ): JellyfinRepository {
         println("Creating new JellyfinRepository")
-        return when (appPreferences.offlineMode) {
+        return when (appPreferences.isOffline) {
             true -> jellyfinRepositoryOfflineImpl
             false -> jellyfinRepositoryImpl
         }
diff --git a/core/src/main/java/com/nomadics9/ananas/viewmodels/DownloadsViewModel.kt b/core/src/main/java/com/nomadics9/ananas/viewmodels/DownloadsViewModel.kt
index f967b91b..a91fc949 100644
--- a/core/src/main/java/com/nomadics9/ananas/viewmodels/DownloadsViewModel.kt
+++ b/core/src/main/java/com/nomadics9/ananas/viewmodels/DownloadsViewModel.kt
@@ -45,7 +45,7 @@ constructor(
     private fun testServerConnection() {
         viewModelScope.launch {
             try {
-                if (appPreferences.offlineMode) return@launch
+                if (appPreferences.isOffline) return@launch
                 repository.getPublicSystemInfo()
                 // Give the UI a chance to load
                 delay(100)
diff --git a/core/src/main/res/values/strings.xml b/core/src/main/res/values/strings.xml
index 9ae2edb5..dd74b8c2 100644
--- a/core/src/main/res/values/strings.xml
+++ b/core/src/main/res/values/strings.xml
@@ -182,6 +182,7 @@
     <string name="cancel_download_message">Are you sure you want to cancel the download?</string>
     <string name="stop_download">Stop download</string>
     <string name="privacy_policy_notice">By using Ananas you agree with the <a href='https://raw.githubusercontent.com/nomadics9/ananas/main/PRIVACY'>Privacy Policy</a> which states that we do not collect any data</string>
+    <string name="turn_on_offline_mode_automatically">Turn on offline mode automatically</string>
     <string name="no_servers_found">No servers found</string>
     <string name="no_users_found">No users found</string>
     <string name="select_user">Select user</string>
diff --git a/core/src/main/res/xml/fragment_settings_network.xml b/core/src/main/res/xml/fragment_settings_network.xml
index 5e5bd8a2..173c0da9 100644
--- a/core/src/main/res/xml/fragment_settings_network.xml
+++ b/core/src/main/res/xml/fragment_settings_network.xml
@@ -1,5 +1,6 @@
 <?xml version="1.0" encoding="utf-8"?>
-<PreferenceScreen xmlns:app="http://schemas.android.com/apk/res-auto">
+<PreferenceScreen xmlns:android="http://schemas.android.com/apk/res/android"
+    xmlns:app="http://schemas.android.com/apk/res-auto">
     <EditTextPreference
         app:defaultValue="30000"
         app:key="pref_network_request_timeout"
@@ -15,4 +16,8 @@
         app:key="pref_network_socket_timeout"
         app:title="@string/settings_socket_timeout"
         app:useSimpleSummaryProvider="true" />
+    <SwitchPreferenceCompat
+        android:defaultValue="false"
+        app:key="pref_auto_offline"
+        app:title="@string/turn_on_offline_mode_automatically" />
 </PreferenceScreen>
\ No newline at end of file
diff --git a/preferences/src/main/java/com/nomadics9/ananas/AppPreferences.kt b/preferences/src/main/java/com/nomadics9/ananas/AppPreferences.kt
index bc1d381c..1dcc1544 100644
--- a/preferences/src/main/java/com/nomadics9/ananas/AppPreferences.kt
+++ b/preferences/src/main/java/com/nomadics9/ananas/AppPreferences.kt
@@ -25,11 +25,27 @@ constructor(
     var offlineMode
         get() = sharedPreferences.getBoolean(Constants.PREF_OFFLINE_MODE, false)
         set(value) {
+            isOffline = value
             sharedPreferences.edit {
                 putBoolean(Constants.PREF_OFFLINE_MODE, value)
             }
         }
 
+    var autoOffline
+        get() = sharedPreferences.getBoolean(Constants.PREF_AUTO_OFFLINE, false)
+        set(value) {
+            sharedPreferences.edit {
+                putBoolean(Constants.PREF_AUTO_OFFLINE, value)
+            }
+        }
+
+    private var _isOffline = sharedPreferences.getBoolean(Constants.PREF_OFFLINE_MODE, false)
+    var isOffline
+        get() = _isOffline
+        set(value) {
+            _isOffline = value
+        }
+
     // Appearance
     val theme get() = sharedPreferences.getString(Constants.PREF_THEME, null)
     val dynamicColors get() = sharedPreferences.getBoolean(Constants.PREF_DYNAMIC_COLORS, true)
diff --git a/preferences/src/main/java/com/nomadics9/ananas/Constants.kt b/preferences/src/main/java/com/nomadics9/ananas/Constants.kt
index a01f49db..6daf599d 100644
--- a/preferences/src/main/java/com/nomadics9/ananas/Constants.kt
+++ b/preferences/src/main/java/com/nomadics9/ananas/Constants.kt
@@ -12,6 +12,7 @@ object Constants {
     // pref
     const val PREF_CURRENT_SERVER = "pref_current_server"
     const val PREF_OFFLINE_MODE = "pref_offline_mode"
+    const val PREF_AUTO_OFFLINE = "pref_auto_offline"
     const val PREF_PLAYER_GESTURES = "pref_player_gestures"
     const val PREF_PLAYER_GESTURES_VB = "pref_player_gestures_vb"
     const val PREF_PLAYER_GESTURES_ZOOM = "pref_player_gestures_zoom"