https://bugs.winehq.org/show_bug.cgi?id=55952
--- Comment #13 from Esme Povirk madewokherd@gmail.com --- I don't think the tests using SocketResponder care about what data the SocketResponder gets, except when requestHandler consumes the data, but it does seem like the expectation is that data sent by SocketResponder can be consumed on the other end, even though it does a Shutdown and Close without verifying that the data has been read.
Given that I haven't seen this specific failure mode before, I think it's unlikely there's a race condition on Windows, but maybe that could be tested by inserting a sleep() in the right place in one of the tests.