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I press play, cloud syncs...but game doesnt start.
I have the same exact problem. on Mac OS Sierra
I ran this in the terminal and it worked:

sudo chmod a+x /Applications/Cuphead.app/Contents/MacOS/Cuphead
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gootik: I ran this in the terminal and it worked:

sudo chmod a+x /Applications/Cuphead.app/Contents/MacOS/Cuphead
thanks, this worked
Post edited October 25, 2018 by davferg
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gootik: I ran this in the terminal and it worked:

sudo chmod a+x /Applications/Cuphead.app/Contents/MacOS/Cuphead
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davferg: thanks, this worked
how to i run it
Off-topic, but can there be a fix for this game to allow support for mods that the Steam version is getting? It doesn't make sense that game that is pretty much the same in terms of file structure as one from another platform but using mods from a different platform than GOG's crashes the game.