diff --git a/src/libraries/System.IO.FileSystem/tests/FileStream/WriteAsync.cs b/src/libraries/System.IO.FileSystem/tests/FileStream/WriteAsync.cs
index 06a9422589ee84..a3077a5e7eb612 100644
--- a/src/libraries/System.IO.FileSystem/tests/FileStream/WriteAsync.cs
+++ b/src/libraries/System.IO.FileSystem/tests/FileStream/WriteAsync.cs
@@ -100,15 +100,27 @@ public async Task SimpleWriteAsync()
             }
         }
 
+        [Fact]
+        public async Task TriggerTheProblemAsync()
+        {
+            if (OperatingSystem.IsWindows())
+            {
+                for (int i = 0; i < 10_000; i++)
+                {
+                    await WriteAsyncCancelledFile(0, FileOptions.Asynchronous | FileOptions.DeleteOnClose);
+                }
+            }
+        }
+
         [Theory]
-        [InlineData(0, true)] // 0 == no buffering
-        [InlineData(4096, true)] // 4096 == default buffer size
-        [InlineData(0, false)]
-        [InlineData(4096, false)]
-        public async Task WriteAsyncCancelledFile(int bufferSize, bool isAsync)
+        [InlineData(0, FileOptions.Asynchronous)] // 0 == no buffering
+        [InlineData(4096, FileOptions.Asynchronous)] // 4096 == default buffer size
+        [InlineData(0, FileOptions.None)]
+        [InlineData(4096, FileOptions.None)]
+        public async Task WriteAsyncCancelledFile(int bufferSize, FileOptions fileOptions)
         {
             const int writeSize = 1024 * 1024;
-            using (FileStream fs = new FileStream(GetTestFilePath(), FileMode.CreateNew, FileAccess.Write, FileShare.None, bufferSize, isAsync))
+            using (FileStream fs = new FileStream(GetTestFilePath(), FileMode.CreateNew, FileAccess.Write, FileShare.None, bufferSize, fileOptions))
             {
                 byte[] buffer = new byte[writeSize];
                 CancellationTokenSource cts = new CancellationTokenSource();
diff --git a/src/libraries/System.Private.CoreLib/src/Microsoft/Win32/SafeHandles/SafeFileHandle.OverlappedValueTaskSource.Windows.cs b/src/libraries/System.Private.CoreLib/src/Microsoft/Win32/SafeHandles/SafeFileHandle.OverlappedValueTaskSource.Windows.cs
index 1ba3516c42a9f1..b0242c679434b6 100644
--- a/src/libraries/System.Private.CoreLib/src/Microsoft/Win32/SafeHandles/SafeFileHandle.OverlappedValueTaskSource.Windows.cs
+++ b/src/libraries/System.Private.CoreLib/src/Microsoft/Win32/SafeHandles/SafeFileHandle.OverlappedValueTaskSource.Windows.cs
@@ -200,6 +200,12 @@ internal void Complete(uint errorCode, uint numBytes)
                 OSFileStreamStrategy? strategy = _strategy;
                 ReleaseResources();
 
+                if (errorCode != Interop.Errors.ERROR_SUCCESS && numBytes != 0)
+                {
+                    _source.SetException(new Exception($"The error code was {errorCode} and numBytes was {numBytes}"));
+                    return;
+                }
+
                 if (strategy is not null && _bufferSize != numBytes) // true only for incomplete operations
                 {
                     strategy.OnIncompleteOperation(_bufferSize, (int)numBytes);