[jrochkind1]

> A while ago you could update a gem and break 3 apps.

You aren't using bundler, are you? You really really should be. It eliminates the vast majority of that class of problem. It's been best practice in Rails, and ruby deployment in general, to use bundler for several years now, it really does make that kind of problem go away.

[bluedino]

We are in our Rails 3 apps.

[jrochkind1]

It is possible to use Bundler even in Rails2 -- if you are getting a lot of pain from that class of problem, it might be worth it.

Although, really, Rails 2.3x stops getting even security updates very soon, it might make more sense to focus all your energy on getting off Rails 2 -- although I know very well how incredibly painful that is. You're in for pain no matter what, sadly.