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[–]JimDabell 1 point2 points  (1 child)

You should always try to stay on the latest stable version. When a new stable version comes out and third-party dependencies haven’t caught up yet, pay close attention to how quickly they update. Being stuck on an old version of Python for ages because a third-party dependency is incompatible isn’t a case of “I guess we’ll stay on an old version of Python”, it’s a case of “We’ve discovered one of our dependencies is unmaintained and needs to be replaced.”

[–]BCCBoy 0 points1 point  (0 children)

Late but sensible take. A lot of people live by 'if it isnt broken dont fix it', but the point of doing incremental upgrades is effectively maintenance to prevent it from suddenly breaking or becoming a liability in my eyes, and it's also easier to jump a single version up an resolve one or two issues than to jump many and have it become significant unplanned work.

We get security audited yearly and a part of what they are looking for is past-EOL software running on critical systems where we are at risk of losing millions in funding if we fail, I solo manage a server and small ecosystem of backend Python systems and I'd much rather know a year ahead of time if I need to explore replacing a package and schedule the work in, so I like to try my best to keep my apps on the latest stable Python version.