diff --git a/v2rayN/ServiceLib/Common/ProcUtils.cs b/v2rayN/ServiceLib/Common/ProcUtils.cs
index ce487c7a..3f5c31af 100644
--- a/v2rayN/ServiceLib/Common/ProcUtils.cs
+++ b/v2rayN/ServiceLib/Common/ProcUtils.cs
@@ -46,7 +46,7 @@ public static class ProcUtils
         return null;
     }
 
-    public static void RebootAsAdmin(bool blAdmin = true)
+    public static bool RebootAsAdmin(bool blAdmin = true)
     {
         try
         {
@@ -58,11 +58,12 @@ public static class ProcUtils
                 FileName = Utils.GetExePath().AppendQuotes(),
                 Verb = blAdmin ? "runas" : null,
             };
-            _ = Process.Start(startInfo);
+            return Process.Start(startInfo) != null;
         }
         catch (Exception ex)
         {
             Logging.SaveLog(_tag, ex);
+            return false;
         }
     }
 }
diff --git a/v2rayN/ServiceLib/Manager/AppManager.cs b/v2rayN/ServiceLib/Manager/AppManager.cs
index 35847d71..7354c305 100644
--- a/v2rayN/ServiceLib/Manager/AppManager.cs
+++ b/v2rayN/ServiceLib/Manager/AppManager.cs
@@ -144,10 +144,16 @@ public sealed class AppManager
         AppEvents.ShutdownRequested.Publish(byUser);
     }
 
-    public async Task RebootAsAdmin()
+    public async Task<bool> RebootAsAdmin()
     {
-        ProcUtils.RebootAsAdmin();
+        var started = ProcUtils.RebootAsAdmin();
+        if (!started)
+        {
+            return false;
+        }
+
         await AppManager.Instance.AppExitAsync(true);
+        return true;
     }
 
     #endregion App
diff --git a/v2rayN/ServiceLib/Services/CoreConfig/Singbox/SingboxOutboundService.cs b/v2rayN/ServiceLib/Services/CoreConfig/Singbox/SingboxOutboundService.cs
index 7a86761f..f422da96 100644
--- a/v2rayN/ServiceLib/Services/CoreConfig/Singbox/SingboxOutboundService.cs
+++ b/v2rayN/ServiceLib/Services/CoreConfig/Singbox/SingboxOutboundService.cs
@@ -345,6 +345,14 @@ public partial class CoreConfigSingboxService
     {
         try
         {
+            // The synthetic TUN relay outbound talks to the local Xray shadowsocks relay.
+            // Xray cannot terminate sing-box h2mux, so muxing here turns local relay traffic
+            // into sp.mux.sing-box.arpa pseudo-destinations and breaks DNS over TUN.
+            if (IsTunRelayProxyOutbound())
+            {
+                return;
+            }
+
             var muxEnabled = _node.MuxEnabled ?? _config.CoreBasicItem.MuxEnabled;
             if (muxEnabled && _config.Mux4SboxItem.Protocol.IsNotEmpty())
             {
@@ -364,6 +372,21 @@ public partial class CoreConfigSingboxService
         }
     }
 
+    private bool IsTunRelayProxyOutbound()
+    {
+        if (!context.IsTunEnabled
+            || _node.ConfigType != EConfigType.Shadowsocks
+            || _node.Address != Global.Loopback
+            || _node.Port != context.ProxyRelaySsPort
+            || _node.Password != Global.None)
+        {
+            return false;
+        }
+
+        var protocolExtra = _node.GetProtocolExtra();
+        return protocolExtra.SsMethod == Global.None;
+    }
+
     private void FillOutboundTls(Outbound4Sbox outbound)
     {
         try
diff --git a/v2rayN/ServiceLib/ViewModels/StatusBarViewModel.cs b/v2rayN/ServiceLib/ViewModels/StatusBarViewModel.cs
index b8154c16..aac51c5c 100644
--- a/v2rayN/ServiceLib/ViewModels/StatusBarViewModel.cs
+++ b/v2rayN/ServiceLib/ViewModels/StatusBarViewModel.cs
@@ -469,31 +469,40 @@ public class StatusBarViewModel : MyReactiveObject
             return;
         }
 
-        _config.TunModeItem.EnableTun = EnableTun;
-
-        if (EnableTun && AllowEnableTun() == false)
+        var allowEnableTun = AllowEnableTun();
+        if (PrepareTunConfigForPrivilegeEscalation(_config, EnableTun, allowEnableTun, Utils.IsWindows()))
         {
-            // When running as a non-administrator, reboot to administrator mode
-            if (Utils.IsWindows())
+            await ConfigHandler.SaveConfig(_config);
+            if (!await AppManager.Instance.RebootAsAdmin())
+            {
+                _config.TunModeItem.EnableTun = false;
+                EnableTun = false;
+                await ConfigHandler.SaveConfig(_config);
+                NoticeManager.Instance.SendMessageEx(ResUI.OperationFailed);
+            }
+            return;
+        }
+
+        if (EnableTun && !allowEnableTun)
+        {
+            bool? passwordResult = await _updateView?.Invoke(EViewAction.PasswordInput, null);
+            if (passwordResult == false)
             {
                 _config.TunModeItem.EnableTun = false;
-                await AppManager.Instance.RebootAsAdmin();
                 return;
             }
-            else
-            {
-                bool? passwordResult = await _updateView?.Invoke(EViewAction.PasswordInput, null);
-                if (passwordResult == false)
-                {
-                    _config.TunModeItem.EnableTun = false;
-                    return;
-                }
-            }
         }
+
         await ConfigHandler.SaveConfig(_config);
         AppEvents.ReloadRequested.Publish();
     }
 
+    private static bool PrepareTunConfigForPrivilegeEscalation(Config config, bool enableTun, bool allowEnableTun, bool isWindows)
+    {
+        config.TunModeItem.EnableTun = enableTun;
+        return enableTun && !allowEnableTun && isWindows;
+    }
+
     private bool AllowEnableTun()
     {
         if (Utils.IsWindows())