diff --git a/src/libraries/System.Net.Http.WinHttpHandler/tests/FunctionalTests/BidirectionStreamingTest.cs b/src/libraries/System.Net.Http.WinHttpHandler/tests/FunctionalTests/BidirectionStreamingTest.cs
index d18de54bc46cbacec7c85e1540d418e9d040a9b4..ce79f20ad4efec7200e022c300a87b19a705d291 100644
--- a/src/libraries/System.Net.Http.WinHttpHandler/tests/FunctionalTests/BidirectionStreamingTest.cs
+++ b/src/libraries/System.Net.Http.WinHttpHandler/tests/FunctionalTests/BidirectionStreamingTest.cs
@@ -143,7 +143,17 @@ public async Task AfterReadResponseServerError_ClientWrite()
                 // Server sends RST_STREAM.
                 await connection.WriteFrameAsync(new RstStreamFrame(FrameFlags.EndStream, 0, streamId));
 
-                await Assert.ThrowsAsync<IOException>(() => requestStream.WriteAsync(new byte[50]).AsTask());
+                await Assert.ThrowsAsync<IOException>(async () =>
+                {
+                    for (int i = 0; i < 10; i++)
+                    {
+                        await requestStream.WriteAsync(new byte[50]);
+
+                        // WriteAsync succeeded because handler hasn't processed RST_STREAM yet.
+                        // Small wait before trying again.
+                        await Task.Delay(50);
+                    }
+                });
             }
         }