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I usually update when I can no longer use the program until I do. Like Spotify. Couldn't listen to music today until I updated...
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I actually went the opposite direction the other day. I bought a used computer with Win XP just for playing games and (for obvious reasons) offline only. Computer games suddenly became fun again! :)
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pro tip, if you mark your network connection as "metered", then windows will be less chattier, and only do security updates or critical bug fixes.
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