When a new Ruby release is incompatible with some versions of your gems dependencies — I think it's time to make a new major release. Old gem versions works with old Bundler and Ruby, new — with new, seems legit.
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Please, update your Rails (or whatever) version or don't update the Ruby. That's all, it's simple.
I’m maintaining multiple gems, so I need to make sure they are compatible with the latest Ruby release.
When a new Ruby release is incompatible with some versions of your gems dependencies — I think it's time to make a new major release. Old gem versions works with old Bundler and Ruby, new — with new, seems legit.