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I have a follow up question, now that I've delved into this more thoroughly. Is this game compatible with Windows 10? I noticed that whenever I try to start the game fresh, it gives me this message which I believe may be the root of the issue! At least, I hope so! :)

I think that's the problem: your PC fears Imscared because it's a "potentially dangerous" application that has not been downloaded much. Try deactivating your firewall (or smartscreen in this case), it should work correctly then :)