Should I be upgrading all my dependencies on a regular basis?

For projects I maintain, I try to keep dependencies up to date on a regular basis. But not all people work like that, some live by the adage of "if it ain't broken don't fix it", but that is not an approach I subscribe to in software development.

A common reason to update software dependencies is to fix security issues or bug fixes that plague the project at hand. My main argument in favour of making more frequent updates is that when you suddenly need to make an update (because of an imminent security threat) it won't be hard; when dependencies haven't been updated in a long time it can be hard to to make the update.

There are risks involved in updating dependencies: A new version might introduce breaking changes, things that you rely on suddenly don't work or exist anymore. It might even introduce new bugs that may not be apparent on the first run. And when your test suite is not on par, verifying if everything works as expected is time consuming. But that can all be address…