Throw HttpSysException with HttpInitialize status details

src/Servers/HttpSys/src/HttpSysListener.cs

@@ -52,7 +52,7 @@ public HttpSysListener(HttpSysOptions options, IMemoryPoolFactory<byte> memoryPo
 
         if (!HttpApi.Supported)
         {
-            throw new PlatformNotSupportedException();
+            throw CreateHttpInitializeFailureException(HttpApi.HttpInitializeStatusCode);
         }
 
         MemoryPool = memoryPoolFactory.Create(new MemoryPoolOptions { Owner = "httpsys" });
@@ -256,6 +256,19 @@ private void DisposeInternal()
         _serverSession.Dispose();
     }
 
+    internal static Exception CreateHttpInitializeFailureException(uint httpInitializeStatusCode)
+    {
+        if (httpInitializeStatusCode == ErrorCodes.ERROR_SUCCESS)
+        {
+            // Keep the existing PlatformNotSupportedException behavior when no specific native error is available.
+            return new PlatformNotSupportedException();
+        }
+
+        return new HttpSysException(
+            (int)httpInitializeStatusCode,
+            $"HttpInitialize failed with status code 0x{httpInitializeStatusCode:X8}.");
+    }
+
     /// <summary>
     /// Accept a request from the incoming request queue.
     /// </summary>

src/Servers/HttpSys/src/NativeInterop/HttpApi.cs

@@ -72,10 +72,12 @@ internal static unsafe uint HttpSetRequestProperty(SafeHandle requestQueueHandle
     internal static bool SupportsClientHello { get; }
     internal static bool SupportsQueryTlsCipherInfo { get; }
     internal static bool Supported { get; }
+    internal static uint HttpInitializeStatusCode { get; }
 
     static unsafe HttpApi()
     {
         var statusCode = PInvoke.HttpInitialize(Version, HTTP_INITIALIZE.HTTP_INITIALIZE_SERVER | HTTP_INITIALIZE.HTTP_INITIALIZE_CONFIG);
+        HttpInitializeStatusCode = statusCode;
 
         if (statusCode == ErrorCodes.ERROR_SUCCESS)
         {

src/Servers/HttpSys/test/Tests/HttpSysListenerTests.cs

@@ -0,0 +1,28 @@
+// Licensed to the .NET Foundation under one or more agreements.
+// The .NET Foundation licenses this file to you under the MIT license.
+
+using Xunit;
+
+namespace Microsoft.AspNetCore.Server.HttpSys;
+
+public class HttpSysListenerTests
+{
+    [Fact]
+    public void CreateHttpInitializeFailureException_WithErrorCode_ReturnsHttpSysExceptionWithDetails()
+    {
+        var errorCode = ErrorCodes.ERROR_ACCESS_DENIED;
+        var exception = Assert.IsType<HttpSysException>(HttpSysListener.CreateHttpInitializeFailureException(errorCode));
+
+        Assert.Contains($"status code 0x{errorCode:X8}", exception.Message);
+        Assert.Equal((int)errorCode, exception.NativeErrorCode);
+    }
+
+    [Fact]
+    public void CreateHttpInitializeFailureException_WithSuccessCode_ReturnsExceptionWithoutInnerException()
+    {
+        var exception = HttpSysListener.CreateHttpInitializeFailureException(ErrorCodes.ERROR_SUCCESS);
+
+        Assert.IsType<PlatformNotSupportedException>(exception);
+        Assert.Null(exception.InnerException);
+    }
+}