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I think there's two sane options:

* track master, and notice breakage as soon as possible (you get much smaller deltas when trying to figure out breakage, which is always a big help), and are able to fix it or report it upstream ASAP, or * hold off slightly till the new release has had more bugs found post-release.

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Main issue is more with other gems that need to be updated as well. It may take take months. You can't do that on your own.

You can't do them all, but you can certainly pitch in and submit patches. Outside rspec-related gems, upgrading usually isn't that hard.

And like all open source, somebody has to do it.

Fork, use your fork, send a pull request. Almost every rails upgrade I make forks and send patches on gems that I need that I forgot about. I get good responsiveness and merge rates. Most of the time a gem needs to be able to support multiple rails versions, so in that case I usually send pull request setting up the Appraisal gem to test for appropriate compatibility.

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