The only times I've ever run into issues updating dependencies (other than across major version upgrades of deeply-integrated deps) is when people have put it off for months or more.
Most updates aren't breaking. The overwhelming majority of updates that are breaking are trivially discovered and fixed with one or two tweaks. Almost all the rest can be fixed with a single search/replace.
Being eight minor versions (or two major versions) behind and having to find and fix all of these at once is when people land themselves into trouble.
Most updates aren't breaking. The overwhelming majority of updates that are breaking are trivially discovered and fixed with one or two tweaks. Almost all the rest can be fixed with a single search/replace.
Being eight minor versions (or two major versions) behind and having to find and fix all of these at once is when people land themselves into trouble.