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Oh gosh, still no success. My first mistake was trying to play games on a Mac lol! Is there anything I can do on my end, or info I could dig up, to make this easier to diagnose? I worry I might have left something out.

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Maybe you can try starting the game through the itch.io app, it seems like a lot of games that have been "unsigned" like mine have the same issue, caused by the macOS Gatekeeper. 

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THAT DID IT!! (Why are Macs so fussy??) Thank you so much for taking the time to help me troubleshoot, I can't wait to play TTwTT