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Re:Upgrading GitHub to Rails 3 with Zero Downtime by jrochkind1 on Monday September 15, 2014 @10:58PM (#8322808)
In my experience, Rails 2->3 was, most decidely, _that bad_. It was the most difficult and frustrating migration I've ever done, and none of the subsequent Rails migrations have been close to as terrible.

(The fact that 2->3 was, like for most, also ruby 1.8 to 1.9 probably contributed)

Re:Upgrading GitHub to Rails 3 with Zero Downtime by dasil003 on Tuesday September 16, 2014 @03:30AM (#8323428)
For me 3.0 -> 3.1 transition was definitely the more painful transition, because it forced me to also do 1.8 -> 1.9 at the same time due to a performance regression that made the test suite jump from 20 minutes to 2.5 hours under 1.8.
Re:Upgrading GitHub to Rails 3 with Zero Downtime by sams99 on Tuesday September 16, 2014 @08:22AM (#8324104)
GitHub are running 2.1.2 GitHub edition Ruby so that is a non-issue for them.

2 -> 3 migration is VERY VERY hard. 3 -> 4 should be relatively easy in comparison.