To Update or Not To Update.

Cover image is of the package.json file from React

I would like to pick brains a little bit and see what your opinion is. My question is:

When you're developing a JS based project, how often do you update your dependencies? It is one thing that drives my OCD absolutely wild and has been a hamper in the past in learning more and making progress.

Do you prefer to wait until the version you're using hits EOL? Until there's a security flaw that you have to patch? Until there's a new major version (assuming it follows SemVer)? Until there's a feature added that you were waiting on? Or do you prefer to be on the bleeding edge?