https://www.screensaversplanet.com/help/guides/mac/how-to-install-johnny-castaway-on-mac-os-x-22
- Install Wineskin
- Create new wrapper with latest(ish) (I used WS11WineCX20.0.2)
- Set wrapper to XP in Tools -> Config Utility
- Download After Dark Tenth Anniversary
- Mount it
- Use install from disk in wrapper (this might fail, I had to copy the files from a Windows VM to get it to fully work)
- Change the following in Tools Registry Editor
- Create a bat file with the following
"C:\WINDOWS\system32\After Dark.scr" /s