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I had issues getting this game to run on El Capitan, and documented my success on another thread. Might help with Sierra as well. https://www.pioneer2.net/community/threads/play-psobb-on-mac-os-x.2352/page-2#post-56659

I ran into this issue. I tried both WineBottler and Wineskin, but couldn't get either to work. The WineBottler version would get to character selection, but would crash when trying to enter a server. The Wineskin version wouldn't run at all. I decided to try using wine from the CLI. I installed...