https://bugs.winehq.org/show_bug.cgi?id=53892
--- Comment #15 from hjlinq@gmail.com --- (In reply to Fabian Maurer from comment #14)
Is that really necessary in order to run 16-bit programs though?
Well, yes... You need 16Bit support to run 16Bit programs. See here for more info: https://cateee.net/lkddb/web-lkddb/X86_16BIT.html
I see. I was hoping 16bit support worked like winevdm (https://github.com/otya128/winevdm)
So it seems my options are either to make a custom Alpine kernel with 16-bit support, or to run winevdm on wine.
I will try and confirm if the issue persists.