When Rails 5 was finally released, I was right in the middle of my first internship with AdWyze. Since this was a breaking release, Ankur Gupta thought it was a good idea for us to board the upgrade train. It is generally a good idea to not get stuck on an older major version of such a big part of your tech stack — just ask Github, who kept using Rails 2.3, till 4 years after the release of Rails 3.x.