https://bugs.winehq.org/show_bug.cgi?id=55852
--- Comment #4 from kadlecf@fzu.cz --- (In reply to Fabian Maurer from comment #3)
Did you try a clean WINEPREFIX? I also had print issues right now, but a clean WINEPREFIX seemed to have fixed it.
As you suggested, I have tried that. The result is essentially the same as before: notepad will print only after the first run on a clean WINEPREFIX. Stopping and restarting notepad is sufficient for the printing to stop working. Clearing the WINEPREFIX directory restores the print functionality again.