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How often do you update your apps?
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Every time there is a new version available for the most part.
I go to the changelog of the app or software to see what has changed, since I only use FOSS I also have a broad glance at the code. If I know that what I am updating won't cause trouble for what I am currently doing (ie. A depency update that is used during a time I need to compile a big project), I go ahead and update.
In the case of new features I am not keen on, I usually keep the current version I have (and make any self-update impossible for said app/software), see if there is any reputable forks or fork it myself to remove said features.
I have a minimal amount of apps and software and I handpicked all of them specifically so that they follow what I want them to do. If for whatever reason they stray and become something I'd rather not use at all, I remove/purge them.
Security is also very important (to me at least). Not updating because a feature is unpleasant is fine as long as the app is fairly recent and has no way of communicating to any other apps or have any internet access.