diff --git a/assets/locales/en.po b/assets/locales/en.po
index e668600711..edacdb9175 100644
--- a/assets/locales/en.po
+++ b/assets/locales/en.po
@@ -1523,3 +1523,15 @@ msgstr "Got it"
 
 msgid "vpn_conflict_connect_anyway"
 msgstr "Connect Anyway"
+
+msgid "err_check_connection"
+msgstr "Unable to connect. Check your internet connection."
+
+msgid "err_service_unavailable"
+msgstr "Service temporarily unavailable. Trying again..."
+
+msgid "err_connection_failed"
+msgstr "Connection failed. Please try again."
+
+msgid "err_ruleset_failed"
+msgstr "Unable to load routing configuration. Retrying..."
diff --git a/lib/core/extensions/error.dart b/lib/core/extensions/error.dart
index c3024a0f45..ba40f2ce3f 100644
--- a/lib/core/extensions/error.dart
+++ b/lib/core/extensions/error.dart
@@ -78,18 +78,69 @@ extension ErrorExetension on Object {
       if (description.contains('Cannot use your own code for promotion')) {
         return "referral_code_own_invalid".i18n;
       }
-      return description;
+
+      final categoryKey = _classifyVpnError(description);
+      if (categoryKey != null) return categoryKey.i18n;
+
+      return "an_error_occurred".i18n;
     }
 
     if (this is StateError) {
-      return (this as StateError).message;
+      final categoryKey = _classifyVpnError((this as StateError).message);
+      if (categoryKey != null) return categoryKey.i18n;
+      return "an_error_occurred".i18n;
     }
     if (this is Exception) {
-      return (this as Exception).toString();
+      final categoryKey = _classifyVpnError((this as Exception).toString());
+      if (categoryKey != null) return categoryKey.i18n;
+      return "an_error_occurred".i18n;
     }
 
-    return "error_occurred".i18n;
+    return "an_error_occurred".i18n;
+  }
+}
+
+/// Classifies VPN-related errors into user-friendly
+/// categories based on regex patterns.
+final List<(RegExp, String)> _vpnErrorPatterns = [
+  (
+    RegExp(
+      r'no such host|dns|network is unreachable|i/o timeout|no route to host|connection refused',
+      caseSensitive: false,
+    ),
+    'err_check_connection',
+  ),
+  (
+    RegExp(r'\b503\b|service unavailable', caseSensitive: false),
+    'err_service_unavailable',
+  ),
+  (
+    RegExp(r'ruleset|geosite|geoip|smart routing', caseSensitive: false),
+    'err_ruleset_failed',
+  ),
+  (
+    RegExp(
+      r'tunnel|tun device|setup failed|failed to start vpn|libbox',
+      caseSensitive: false,
+    ),
+    'err_connection_failed',
+  ),
+];
+
+String? _classifyVpnError(String description) {
+  if (description.isEmpty) return null;
+  for (final (pattern, key) in _vpnErrorPatterns) {
+    if (pattern.hasMatch(description)) return key;
   }
+  return null;
+}
+
+/// Returns a localized user-facing message for a raw error string. Use this
+/// at boundaries where errors arrive as plain strings (e.g. FFI results)
+/// rather than as `Exception` instances, instead of wrapping them in
+/// `Exception(...)` just to route through `localizedDescription`.
+String localizeRawError(String rawError) {
+  return (_classifyVpnError(rawError) ?? 'an_error_occurred').i18n;
 }
 
 /// Strips the radiance IPC prefix from error messages.
diff --git a/lib/core/services/app_purchase.dart b/lib/core/services/app_purchase.dart
index 0f01fd3727..69ca1e4178 100644
--- a/lib/core/services/app_purchase.dart
+++ b/lib/core/services/app_purchase.dart
@@ -309,7 +309,7 @@ class AppPurchase {
     final fetchResult = await lanternService.fetchUserData();
     final fetchedUser = fetchResult.fold((failure) {
       appLogger.warning(
-        '[AppPurchase] Failed to fetch latest user data for purchase check: ${failure.localizedErrorMessage}',
+        '[AppPurchase] Failed to fetch latest user data for purchase check: ${failure.error}',
       );
       return null;
     }, (user) => user);
@@ -317,7 +317,7 @@ class AppPurchase {
     final user = fetchedUser ??
         (await lanternService.getUserData()).fold((failure) {
           appLogger.warning(
-            '[AppPurchase] Failed to load cached user data for purchase check: ${failure.localizedErrorMessage}',
+            '[AppPurchase] Failed to load cached user data for purchase check: ${failure.error}',
           );
           return null;
         }, (user) => user);
diff --git a/lib/features/account/account.dart b/lib/features/account/account.dart
index 4868fc1d6e..458d3a2e7d 100644
--- a/lib/features/account/account.dart
+++ b/lib/features/account/account.dart
@@ -437,7 +437,7 @@ class Account extends HookConsumerWidget {
     result.fold(
       (l) {
         context.hideLoadingDialog();
-        appLogger.error('Logout error: ${l.localizedErrorMessage}');
+        appLogger.error('Logout error: ${l.error}');
         context.showSnackBar(l.localizedErrorMessage);
       },
       (user) {
diff --git a/lib/features/account/delete_account.dart b/lib/features/account/delete_account.dart
index 7ec12ace12..f077197748 100644
--- a/lib/features/account/delete_account.dart
+++ b/lib/features/account/delete_account.dart
@@ -171,7 +171,7 @@ class _DeleteAccountState extends ConsumerState<DeleteAccount> {
     result.fold(
       (failure) {
         appLogger
-            .error('Account deletion failed: ${failure.localizedErrorMessage}');
+            .error('Account deletion failed: ${failure.error}');
         context.hideLoadingDialog();
         context.showSnackBarError(failure.localizedErrorMessage);
       },
diff --git a/lib/features/auth/choose_payment_method.dart b/lib/features/auth/choose_payment_method.dart
index ab79b877e5..935f96379f 100644
--- a/lib/features/auth/choose_payment_method.dart
+++ b/lib/features/auth/choose_payment_method.dart
@@ -215,6 +215,7 @@ class ChoosePaymentMethod extends HookConsumerWidget {
           },
           onError: (error) {
             finishPaymentRedirect(paymentRedirectInFlight);
+
             ///error while subscribing
             appLogger.error('Error subscribing to plan: $error');
             if (error is StripeException) {
@@ -322,9 +323,7 @@ class ChoosePaymentMethod extends HookConsumerWidget {
       await result.fold<Future<void>>(
         (failure) async {
           context.hideLoadingDialog();
-          appLogger.error(
-            'Error redirecting to payment: ${failure.localizedErrorMessage}',
-          );
+          appLogger.error('Error redirecting to payment: ${failure.error}');
           context.showSnackBar(failure.localizedErrorMessage);
         },
         (url) async {
diff --git a/lib/features/auth/create_password.dart b/lib/features/auth/create_password.dart
index 900faed08b..17b1debc23 100644
--- a/lib/features/auth/create_password.dart
+++ b/lib/features/auth/create_password.dart
@@ -104,7 +104,7 @@ class CreatePassword extends HookConsumerWidget {
       (failure) {
         context.hideLoadingDialog();
         appLogger.error(
-          'Failed to create password: ${failure.localizedErrorMessage}',
+          'Failed to create password: ${failure.error}',
         );
         context.showSnackBarError(failure.localizedErrorMessage);
       },
diff --git a/lib/features/home/provider/feature_flag_notifier.dart b/lib/features/home/provider/feature_flag_notifier.dart
index 4e14a46783..4ad098232e 100644
--- a/lib/features/home/provider/feature_flag_notifier.dart
+++ b/lib/features/home/provider/feature_flag_notifier.dart
@@ -20,7 +20,7 @@ class FeatureFlagNotifier extends _$FeatureFlagNotifier {
     result.fold(
       (failure) {
         appLogger.error(
-            'Error fetching feature flags: ${failure.localizedErrorMessage}');
+            'Error fetching feature flags: ${failure.error}');
       },
       (flags) {
         try {
diff --git a/lib/features/home/provider/home_notifier.dart b/lib/features/home/provider/home_notifier.dart
index 4461da9881..af7a814f86 100644
--- a/lib/features/home/provider/home_notifier.dart
+++ b/lib/features/home/provider/home_notifier.dart
@@ -20,7 +20,7 @@ class HomeNotifier extends _$HomeNotifier {
     return result.fold(
       (failure) {
         appLogger.error(
-          'Error getting user data: ${failure.localizedErrorMessage}',
+          'Error getting user data: ${failure.error}',
         );
         throw Exception('Failed to get user data');
       },
@@ -38,7 +38,7 @@ class HomeNotifier extends _$HomeNotifier {
     result.fold(
       (failure) {
         appLogger.error(
-          'Error fetching user data: ${failure.localizedErrorMessage}',
+          'Error fetching user data: ${failure.error}',
         );
       },
       (userData) {
@@ -56,7 +56,7 @@ class HomeNotifier extends _$HomeNotifier {
     result.fold(
       (failure) {
         appLogger.error(
-          'Error refreshing user data: ${failure.localizedErrorMessage}',
+          'Error refreshing user data: ${failure.error}',
         );
         state = AsyncValue.error(failure, StackTrace.current);
       },
diff --git a/lib/features/language/language.dart b/lib/features/language/language.dart
index dc8bdcfb0f..f52f6942bb 100644
--- a/lib/features/language/language.dart
+++ b/lib/features/language/language.dart
@@ -104,7 +104,7 @@ class LanguageListView extends HookConsumerWidget {
       either.fold(
         (failure) {
           appLogger
-              .error('Error updating locale: ${failure.localizedErrorMessage}');
+              .error('Error updating locale: ${failure.error}');
         },
         (r) {
           appLogger.debug('Locale updated to: $newLocale');
diff --git a/lib/features/macos_extension/macos_extension_dialog.dart b/lib/features/macos_extension/macos_extension_dialog.dart
index 4fe481fabd..865cc227ec 100644
--- a/lib/features/macos_extension/macos_extension_dialog.dart
+++ b/lib/features/macos_extension/macos_extension_dialog.dart
@@ -141,7 +141,7 @@ class _MacOSExtensionDialogState extends ConsumerState<MacOSExtensionDialog> {
 
     result.fold(
       (failure) {
-        appLogger.error("Failure: ${failure.localizedErrorMessage}");
+        appLogger.error("Failure: ${failure.error}");
         AppDialog.errorDialog(
           context: context,
           title: 'error'.i18n,
diff --git a/lib/features/plans/provider/plans_notifier.dart b/lib/features/plans/provider/plans_notifier.dart
index 44d8701ac3..c341bab680 100644
--- a/lib/features/plans/provider/plans_notifier.dart
+++ b/lib/features/plans/provider/plans_notifier.dart
@@ -93,7 +93,6 @@ class PlansNotifier extends _$PlansNotifier {
   }
 
   void setSelectedPlan(Plan plan) {
-    appLogger.info('[PlansNotifier] setSelectedPlan: ${plan.id}');
     userSelectedPlan = plan;
   }
 
diff --git a/lib/features/private_server/manually_server_setup.dart b/lib/features/private_server/manually_server_setup.dart
index d7a5c9fff8..0a309b7ef8 100644
--- a/lib/features/private_server/manually_server_setup.dart
+++ b/lib/features/private_server/manually_server_setup.dart
@@ -181,7 +181,7 @@ class _ManuallyServerSetupState extends ConsumerState<ManuallyServerSetup> {
     result.fold(
       (failure) {
         appLogger
-            .error("Failed to add server: ${failure.localizedErrorMessage}");
+            .error("Failed to add server: ${failure.error}");
         context.hideLoadingDialog();
         context.showSnackBar(failure.localizedErrorMessage);
       },
diff --git a/lib/features/private_server/private_server_deploy.dart b/lib/features/private_server/private_server_deploy.dart
index 8f6fb6e5f8..0010f2384f 100644
--- a/lib/features/private_server/private_server_deploy.dart
+++ b/lib/features/private_server/private_server_deploy.dart
@@ -179,7 +179,7 @@ class _PrivateServerDeployState extends ConsumerState<PrivateServerDeploy> {
         context.hideLoadingDialog();
         // Handle failure case, e.g., show an error message
         appLogger
-            .error("Failed to cancel deployment: ${l.localizedErrorMessage}");
+            .error("Failed to cancel deployment: ${l.error}");
         context.showSnackBar(l.localizedErrorMessage);
       },
       (r) {
diff --git a/lib/features/system_tray/provider/system_tray_notifier.dart b/lib/features/system_tray/provider/system_tray_notifier.dart
index 06c6bcf0ea..7779e32b49 100644
--- a/lib/features/system_tray/provider/system_tray_notifier.dart
+++ b/lib/features/system_tray/provider/system_tray_notifier.dart
@@ -128,7 +128,7 @@ class SystemTrayNotifier extends _$SystemTrayNotifier with TrayListener {
         .connectToServer(ServerLocationType.lanternLocation, server.tag);
     result.fold(
       (failure) => appLogger.error(
-        'Failed to connect: ${failure.localizedErrorMessage}',
+        'Failed to connect: ${failure.error}',
       ),
       (success) {
         appLogger.info('Connecting to ${server.location.country} - ${server.location.city}');
diff --git a/lib/features/vpn/provider/available_servers_notifier.dart b/lib/features/vpn/provider/available_servers_notifier.dart
index fcfe42b396..1294c23466 100644
--- a/lib/features/vpn/provider/available_servers_notifier.dart
+++ b/lib/features/vpn/provider/available_servers_notifier.dart
@@ -16,7 +16,7 @@ class AvailableServersNotifier extends _$AvailableServersNotifier {
     return result.fold(
       (failure) {
         appLogger.error(
-          'Error getting available servers: ${failure.localizedErrorMessage}',
+          'Error getting available servers: ${failure.error}',
         );
         throw Exception('Failed to load available servers');
       },
@@ -40,7 +40,7 @@ class AvailableServersNotifier extends _$AvailableServersNotifier {
     result.fold(
       (failure) {
         appLogger.error(
-          'Error getting available servers: ${failure.localizedErrorMessage}',
+          'Error getting available servers: ${failure.error}',
         );
       },
       (servers) {
diff --git a/lib/features/vpn/server_selection.dart b/lib/features/vpn/server_selection.dart
index 8386c6129d..4c0480d5d2 100644
--- a/lib/features/vpn/server_selection.dart
+++ b/lib/features/vpn/server_selection.dart
@@ -239,7 +239,7 @@ class _ServerSelectionState extends ConsumerState<ServerSelection> {
               retryResult.fold((failure) {
                 context.showSnackBar(failure.localizedErrorMessage);
                 appLogger.error(
-                  "Error changing VPN state: ${failure.localizedErrorMessage}",
+                  "Error changing VPN state: ${failure.error}",
                 );
               }, (_) => appRouter.popUntilRoot());
             },
diff --git a/lib/features/vpn/vpn_switch.dart b/lib/features/vpn/vpn_switch.dart
index 057d6b0e30..bb5f1920c5 100644
--- a/lib/features/vpn/vpn_switch.dart
+++ b/lib/features/vpn/vpn_switch.dart
@@ -113,7 +113,7 @@ class VPNSwitch extends HookConsumerWidget {
                 (failure) {
                   context.showSnackBar(failure.localizedErrorMessage);
                   appLogger.error(
-                      "Error changing VPN state: ${failure.localizedErrorMessage}");
+                      "Error changing VPN state: ${failure.error}");
                 },
                 (_) => null,
               );
@@ -122,7 +122,7 @@ class VPNSwitch extends HookConsumerWidget {
         } else {
           context.showSnackBar(failure.localizedErrorMessage);
           appLogger.error(
-              "Error changing VPN state: ${failure.localizedErrorMessage}");
+              "Error changing VPN state: ${failure.error}");
         }
       },
       (_) => null,
diff --git a/lib/lantern/lantern_ffi_service.dart b/lib/lantern/lantern_ffi_service.dart
index a533960699..cc114b4522 100644
--- a/lib/lantern/lantern_ffi_service.dart
+++ b/lib/lantern/lantern_ffi_service.dart
@@ -523,7 +523,12 @@ class LanternFFIService implements LanternCoreService {
         // Not JSON — fall through with the raw string.
       }
       appLogger.error('$action split tunnel error: $errMsg');
-      return left(Failure(error: errMsg, localizedErrorMessage: errMsg));
+      return left(
+        Failure(
+          error: errMsg,
+          localizedErrorMessage: localizeRawError(errMsg),
+        ),
+      );
     } catch (e) {
       return left(
         Failure(
@@ -589,7 +594,13 @@ class LanternFFIService implements LanternCoreService {
         }
       });
       if (result.isNotEmpty && !_ffiOkResults.contains(result)) {
-        return left(Failure(error: result, localizedErrorMessage: result));
+        appLogger.error('startVPN error: $result');
+        return left(
+          Failure(
+            error: result,
+            localizedErrorMessage: localizeRawError(result),
+          ),
+        );
       }
       appLogger.debug('startVPN result: $result');
       return right(result.isEmpty ? 'ok' : result);
@@ -670,7 +681,13 @@ class LanternFFIService implements LanternCoreService {
         }
       });
       if (result.isNotEmpty && !_ffiOkResults.contains(result)) {
-        return left(Failure(error: result, localizedErrorMessage: result));
+        appLogger.error('stopVPN error: $result');
+        return left(
+          Failure(
+            error: result,
+            localizedErrorMessage: localizeRawError(result),
+          ),
+        );
       }
       appLogger.debug('stopVPN result: $result');
       return right(result.isEmpty ? 'ok' : result);
diff --git a/test/core/models/app_setting_auth_session_test.dart b/test/core/models/app_setting_auth_session_test.dart
deleted file mode 100644
index d95b55f007..0000000000
--- a/test/core/models/app_setting_auth_session_test.dart
+++ /dev/null
@@ -1,46 +0,0 @@
-import 'package:flutter_test/flutter_test.dart';
-import 'package:lantern/core/models/app_setting.dart';
-
-void main() {
-  group('AppSetting.clearAuthSessionData', () {
-    test('clears auth/session fields by default', () {
-      const before = AppSetting(
-        isPro: true,
-        userLoggedIn: true,
-        oAuthToken: 'token-123',
-        oAuthLoginProvider: 'google',
-        email: 'user@example.com',
-        environment: 'stage',
-        locale: 'en_US',
-      );
-
-      final after = before.clearAuthSessionData();
-
-      expect(after.isPro, isFalse);
-      expect(after.userLoggedIn, isFalse);
-      expect(after.oAuthToken, isEmpty);
-      expect(after.oAuthLoginProvider, isEmpty);
-      expect(after.email, isEmpty);
-      expect(after.environment, equals('stage'));
-      expect(after.locale, equals('en_US'));
-    });
-
-    test('can preserve email when requested', () {
-      const before = AppSetting(
-        isPro: true,
-        userLoggedIn: true,
-        oAuthToken: 'token-123',
-        oAuthLoginProvider: 'apple',
-        email: 'user@example.com',
-      );
-
-      final after = before.clearAuthSessionData(clearEmail: false);
-
-      expect(after.isPro, isFalse);
-      expect(after.userLoggedIn, isFalse);
-      expect(after.oAuthToken, isEmpty);
-      expect(after.oAuthLoginProvider, isEmpty);
-      expect(after.email, equals('user@example.com'));
-    });
-  });
-}