https://bugs.winehq.org/show_bug.cgi?id=52773
--- Comment #4 from Austin English austinenglish@gmail.com --- I've definitely seen this and remember working around it by running` wineserver -w` after `wineboot` to make sure things were settled before continuing.
That said, I'm on mobile, can't remember if there's a bug for this or if I've bisected it..