Before choosing an installation method, it helps to understand why AA2 is notoriously difficult to run on Mac:
There is a known Wine installer for AA2 on Lutris , which uses the "AA2MiniPPX" repack—a minimal version of the game with AAUnlimited pre-installed. However, running AA2 through raw Wine requires several steps: Artificial Academy 2 Mac
In Wineskin Advanced settings, point the Windows EXE path directly to AA2Play.exe . Before choosing an installation method, it helps to
Due to the game's age (2014) and its reliance on legacy DirectX 9 calls, running it on modern Macs requires translation or virtualization. Before choosing an installation method
The popular (by Meteors) modifies game DLLs and adds Japanese/English translations. It partially works via Wine: