https://bugs.winehq.org/show_bug.cgi?id=38838
--- Comment #27 from Andrew Eikum aeikum@codeweavers.com --- The issue seems to be the osppsvc background service doesn't finish writing its activation data to tokens.dat before it is killed by prefix shutdown. When this file is corrupt, it tries again, and that's what you see when you launch a program and see the Setup dialog. It then asks you to reboot, and that causes the prefix to shutdown before it has finished writing that file, again.
If you keep the prefix alive for ~20 seconds after installation is complete, or after that Setup dialog claims completion, then the service will finish writing the file and subsequent launches should work.
I'm looking into solutions.