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Clicking play, computer thinks, button grays out, play button is clickable again. Tried repair, tried reinstalling, tried changing compatibility. No dice. Google gave me a thread from a long time ago with a person with the same issue, no responses. :(

Windows 10
Gog galaxy 2.0.68.112 beta
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I haven't used Windows for many years, but there are a few suggestions I still remember. First, have you run scandisk, to make sure everything's OK? Second the same question, but with defrag instead. Often, that's all you need to fix issues like this.
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Guybrushlol: Clicking play, computer thinks, button grays out, play button is clickable again. Tried repair, tried reinstalling, tried changing compatibility. No dice. Google gave me a thread from a long time ago with a person with the same issue, no responses. :(

Windows 10
Gog galaxy 2.0.68.112 beta
Have you tried running from the game's .exe instead of from Galaxy?