diff --git a/src/coreclr/System.Private.CoreLib/src/System/StubHelpers.cs b/src/coreclr/System.Private.CoreLib/src/System/StubHelpers.cs
index 3d5f7da15005ef..e5545635ba3172 100644
--- a/src/coreclr/System.Private.CoreLib/src/System/StubHelpers.cs
+++ b/src/coreclr/System.Private.CoreLib/src/System/StubHelpers.cs
@@ -972,9 +972,18 @@ public override unsafe IntPtr ConvertToNative(object managed, int dwFlags)
                 int allocSize = Marshal.SizeOfHelper((RuntimeType)_layoutType, false);
                 IntPtr pNative = Marshal.AllocCoTaskMem(allocSize);
 
-                if (IsIn(dwFlags))
+                try
                 {
-                    StubHelpers.LayoutTypeConvertToUnmanaged(managed, (byte*)pNative, ref _cleanupWorkList);
+                    if (IsIn(dwFlags))
+                    {
+                        StubHelpers.LayoutTypeConvertToUnmanaged(managed, (byte*)pNative, ref _cleanupWorkList);
+                    }
+                }
+                catch
+                {
+                    StubHelpers.DestroyCleanupList(ref _cleanupWorkList);
+                    Marshal.FreeCoTaskMem(pNative);
+                    throw;
                 }
 
                 return pNative;
diff --git a/src/tests/Interop/PInvoke/AsAny/AsAnyTest.cs b/src/tests/Interop/PInvoke/AsAny/AsAnyTest.cs
index f53a66919e1cf1..d8f68093574de8 100644
--- a/src/tests/Interop/PInvoke/AsAny/AsAnyTest.cs
+++ b/src/tests/Interop/PInvoke/AsAny/AsAnyTest.cs
@@ -318,6 +318,7 @@ public static int TestEntryPoint()
             TestIntPtrArray();
             TestUIntPtrArray();
             TestLayout();
+            TestLayoutConvertToNativeExceptionPath();
             RunAsAnyFieldTests();
             TestUnicodeString();
             TestUnicodeStringArray();
@@ -654,6 +655,16 @@ public static void TestLayout() {
         Console.WriteLine("------------------------");
     }
 
+    private static void TestLayoutConvertToNativeExceptionPath()
+    {
+        // AsAnyField contains a field with [MarshalAs(UnmanagedType.AsAny)], which is not
+        // supported in layout marshaling. When passed via AsAny, LayoutImplementation.ConvertToNative
+        // allocates a native buffer and then calls LayoutTypeConvertToUnmanaged, which throws
+        // TypeLoadException. Verify the exception propagates correctly; the fix ensures the
+        // native buffer is freed on this exception path rather than leaked.
+        Assert.Throws<TypeLoadException>(() => PassLayout(new AsAnyField()));
+    }
+
     static void CharArrayInit(char[] unMappableCharArray_In, char[] unMappableCharArray_InOut, char[] unMappableCharArray_Out,
         char[] mappableCharArray_In, char[] mappableCharArray_InOut, char[] mappableCharArray_Out,
         string unMappableStr, string mappableStr)