I do agree with more frequent upgrades, but it has to be part of the culture. The longer you wait, the harder it gets. Unfortunately, I have worked in some heavily tech-debt-laden environments where upgrading anything required an act of god. I've logged on to production servers with 1500+ days of uptime at multiple companies. Nothing had been updated since well before that time. At one place, I recall encountering a 10+ year old dependency. On top of that, they were still using Python 2.7. This wasn't that long ago.