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I upgraded to windows 11 by accidentally pressing spacebar on startup
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I dual boot windows because of a few things that don't matter too much to me, and i haven't really figured out wine as much as i should. Anyway, i booted up windows again after like 5 months. I hated every second of it, but overall, nothing of note happened. The next day, i had to boot windows again, and when i shut it down, it gave me the option to update and reboot or update and shut down, nothing else. I should've just unplugged my pc, but I updated and shut it down and left my room. When i came back a few hours later, my pc was stuck in a reboot loop and i couldn't really boot anything. Just fuck everything about windows.
I would honestly suggest using Lutris or Bottles as a convenient interface for Wine, rather than trying to figure out Wine itself.
Lots of convenient features and pretty turnkey, depending on what you're trying to install.
I set up a "Bottles" setup for older 90's-00's games and, know what? Sims 1 ran perfectly. Was mind blowing. (Notoriously difficult to run on modern windows)
Hope that is somewhat encouraging!
If you dual boot, you need to keep the windows partition on a separate disk, otherwise it will most likely fuck your boot partition.
Honestly disconnect all other disks when installing it too. Otherwise you move your Linux disk to another computer and Windows might not boot because it decided to use the efi partition on your Linux disk
In 20 years of using Linux, I've only had a broken Linux four times. Four of those times, it was because of Windows being shit.