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Yehuda lays out some of the history and rationale behind Rubygems’s multi-package-version design and also takes a look at how a few recent tools (Bundler, Rip, rvm, etc.) are using different approaches to develop concepts around multiple “environments”.

I’ve never been a fan of Rubygems multi-versioned, directory-per-package approach to organizing packages. There’s a few different reasons, but mostly it forces a lot of unnecessary complexity into runtime that could (I think) be handled more simply at install time. I do like the convenience of installing a bunch of packages into a single Rubygems environment without having to think about it, but those benefits are outweighed by the subtle differences in runtime behavior, some of which can be extremely annoying (e.g., “already activated” errors). I’d rather be aware of and be forced to deal with those issues at install time. It’s great to see so much experimentation on new tools and alternative approaches.