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So why did for example Ruby not have such a painful transition from 1.8 to 1.9/2.0? My theory is that the Ruby people make the migration in many steps, it started even back in at least Ruby 1.8.6 and they did it with a lot of care on how to make the transition as painless as possible while the Python team just broke everything and bet on that tools like 2to3 would just magically solve it.

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Right. I think a key miss was underestimating value of code that would work w both 2 and 3. This avoids need to upgrade all at once.

Relax things a tiny bit in 3, back port to 2 via futures, get a library like six going. It could have been a ton easier.

In fairness by 3.5 maybe they’d realized this, but a lot of lecturing was done before. Initially recommendation was to upgrade all dependencies and programs to 3 and not try and make dependencies work w both

I think rubys TDD culture at the time also probably helped. My (purely unsupported) opinion is that the test suites were likely more fleshed out on ruby so its less of a risk to switch. That said, I still saw lots of 1.8.6 installs in the wild for quite some time after 2.0 hit.

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