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Couldn't help but notice the irony behind this post in your "Previous Posts" section: https://martinhering.me/post/0/everything-thats-wrong-with-h...

Also, I've always been curious what the process for upgrading to new OS versions on a Hackintosh is like. Is it expected that once you get the machine in a working state, you are better off not to touch it?

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I used to image my boot disk before each update, saved me a few times when I needed the machine to just work again.

Then moved to Linux in 2013, never needed to go back.

You can upgrade like you would on normal mac hardware

…but things often break, do they not?

For major releases like sierra -> high sierra it pays to wait 2-3 weeks and check around on forums for any issues. I had a few issues with some drivers going from Yosemite to El Capitan. My Sierra to High Sierra upgrade had no issues though. I have noticed bugs in the upgrade process have generally declined pretty steadily since I first started hackintoshing with Mavericks.

I never had any issues with minor releases with Sierra or High Sierra.

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