https://bugs.winehq.org/show_bug.cgi?id=57926
--- Comment #2 from Esme Povirk madewokherd@gmail.com --- Actually, I don't think this is caused by the wpfclipboard test doing weird things. This appears to be entirely contained in WPF's CriticalSetDataObject method, which would mean it's not unlikely for this to happen in normal use.
And it seems WPF is making this more likely by inserting a 0.1 second Sleep call between setting the clipboard and calling OleFlushClipboard. This makes it even less likely that it's broken in this way on Windows.