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> If you're not updating, it may not work with the latest version of ruby/rails/whatever.

Do Ruby/Rails/whoever often have releases that break backwards compatibility?

Some gems don't function correctly with Ruby 1.9.1, and a lot have minor issues with Rails 3.

Although sometimes it's more an issue with the documentation as opposed to code issues.

It varies, re: Ruby, moving from 1.8 to 1.9 (the latter of which is basically the difference between major versions, though for some reason they aren't calling it 2.0). I think things are worse in this regard for Rails than for Ruby.

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