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Running unlisted .exe "returns 255"

I'm on the latest version Catalina. I'm trying to run this program here:
https://github.com/coczero/Last.fm-Scrubbler-WPF

I installed CrossOver, created a bottle for an unknown app using the Last.fm app's folder (the program doesn't have a dedicated installer file), then tried to run the .exe file; I got the message "The command [directory] returned 255."

What does this mean, and how do I get this app to run? I was able to do this kind of thing perfectly with plain old WINE in the past, and now it seems to be... not so perfect.

The enhanced GateKeeper security in Catalina can cause some issues. One of these is an error like you are seeing. You need to manually unblock the application so it can run. Once you try to run the application, go to System Preferences, then Security & Privacy. In the General tab, you should see a button near the bottom to "unblock" the application. Once you click on that, it will allow the application to load. Keep in mind that it may trigger on other DLLs and such, so you might want to keep that window open when you launch the application so you can unblock anything else it catches.

I know that this thread is a little old, but I'm running into the same problem with Big Sur. Unfortunately there is no option for me to unlock the application in Security & Privacy...

Is there any other way to solve this?

I'm also on Big Sur and having the exact same problem. I've tried allowing my Mac to open Applications from anyone from the Terminal but that doesn't work either. Would really love some help.

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