Running macOS Sierra(Version 10.12.2 16C67).

I installed Wine version wine-1.8.6 (through a .pkg file). I opened up a game and it worked fine.

The next day when I downloaded Origin installer, it wouldn't open. When I double clicked on it, the Wine icon showed up in the dock and said it was open, but no windows showed up. When I clicked on another program(or on the desktop), Wine closed. Now when I try to start that same game I opened when I first installed Wine, the same thing happens that happened when I started Origin installer.

When I go to the terminal and type wine {path of .exe} I got this: enter image description here

I installed wine tricks using brew install winetricks and it installed fine, yet it didn't change my situation.

winecfg works properly, and so does sh winetricks.


The real problem was that I had removed the Z: drive which pointed to my root directory. After adding the Z: drive back using winecfg, I was able to run Windows programs from any location again.

image showing Z: drive pointing to root directory in winecfg

I finally got it fixed. I just deleted the .wine folder, ran winecfg again, and everything started working.

rm -rf ~/.wine

Sometimes after trying this solution, I still have this problem. I have found that moving the program to inside the ~/.wine/drive_c folder fixes this.

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You can consider installing Wine.app via brew-cask, e.g.

brew cask install wine-stable

By using the macOS app, it can handle executable and file locations in a better way.

There is also the WineBottler app which comes with Wine.app as well.

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