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Well, the most vocal ruby community was RoR users, while python even back then was used by multiple camps.

Ruby done a smart upgrade path - new features in 2.x and breaking changes in 1.9.x. Ruby also got a "new" VM (it wasn't new, but it was the new default VM).

Before 1.9.3 the best way to deploy ruby was Passenger with RubyEE. RubyEE was based on 1.8.7 and with all the improvements that the mainline ruby implementation got there was no reason to maintain RubyEE fork. The 2.0.0 release meant to be 100% compatible with 1.9.3 and had ABI version 1.9.1.

Also, prior 2.1.0 Ruby used versioning very different from SemVer, hence 1.9.x had multiple breaking changes in its lifetime. It didn't mean "patch" version back then.

I think the main difference is that the newer ruby was actually faster than the older ruby and gave plenty of reasons to move. The main pain point im ruby migration was that it became encoding aware. Python 3 wasn't as lucky.



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