https://bugs.winehq.org/show_bug.cgi?id=43355
--- Comment #10 from ads200002@gmail.com --- Can confirm that this is a regression in Wine 2.8 (or, at least, Wine 2.7 Staging works). To get AoE II HD working on Mac, try using the PlayOnMac installer, rename the launcher, and change the Wine version to 2.7 Staging (i386).