Update from OS X 10.8.5 to macOS
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Solved by maplepants,
Your Mac should be able to run High Sierra, but upgrading from Mountain Lion via the App Store might not work.
So I'd recommend you backup your data then download High Sierra: http://updates-http.cdn-apple.com/2019/cert/061-39476-20191023-48f365f4-0015-4c41-9f44-39d3d2aca067/InstallOS.dmg
Create an install disk and install it on your Mac.
Once done, install High Sierra via the App Store: macappstores://apps.apple.com/app/macos-high-sierra/id1246284741?mt=12.
Those links are from here: https://support.apple.com/en-us/HT211683 which also contains more info that might help.
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