At my last job, we only updated dependencies when there was a compelling reason. It was awful.

What would happen from time to time was that an important reason did come up, but the team was now many releases behind. Whoever was unlucky enough to sign up for the project that needed the updated dependency now had to do all those updates of the dependency, including figuring out how they affected a bunch of software that they weren't otherwise going to work on. (e.g., for one code path, I need a bugfix that was shipped three years ago, but pulling that into my component affects many other code paths.) They now had to go figure out what would break, figure out how to test it, etc. Besides being awful for them, it creates bad incentives (don't sign up for those projects; put in hacks to avoid having to do the update), and it's also just plain bad for the business because it means almost any project, however simple it seems, might wind up running into this pit.

I now think of it this way: either you're on the dependency's release train or you jump off. If you're on the train, you may as well stay pretty up to date. It doesn't need to be every release the minute it comes out, but nor should it be "I'll skip months of work and several major releases until something important comes out". So if you decline to update to a particular release, you've got to ask: am I jumping off forever, or am I just deferring work? If you think you're just deferring the decision until you know if there's a release worth updating to, you're really rolling the dice.

(edit: The above experience was in Node.js. Every change in a dynamically typed language introduces a lot of risk. I'm now on a team that uses Rust, where knowing that the program compiles and passes all tests gives us a lot of confidence in the update. So although there's a lot of noise with regular dependency updates, it's not actually that much work.)

I think it also depends on the community as well. Last time I touched Node.js and Javascript-related things, every time I tried to update something, it practically guaranteed something would explode for no reason.

While my recent legacy Java project migration from JDK 8 -> 21 & a ton of dependency upgrades has been a pretty smooth experience so far.

> I'm now on a team that uses Rust, where knowing that the program compiles and passes all tests gives us a lot of confidence in the update.

That's been my experience as well. In addition, the ecosystem largely holds to semver, which means a non-major upgrade tends to be painless, and conversely, if there's a major upgrade, you know not to put it off for too long because it'll involve some degree of migration.

My current employer publishes "staleness" metrics at the project level. It's imperfect because it weights all the dependencies the same, but it's better than nothing.

Update at least quarterly so you don’t have them stale an super hard to update