1. Absolutely no tests of any kind
2. Over 100 gem dependencies
Upgrade from 3.2.x to 4.2.x took one developer (me) three weeks of work. I don't know if that's a lot or not, given the major version upgrade and all of the gems (which were a huge pain). I've not had any problems in production reported via Honeybadger or by end users, so I think the upgrade was a success. I did end up writing about 200 unit and integration specs during the process.
I'm thinking back to my days in the .Net world at BigCorp. Unfortunately I have nothing to compare it to, because we never upgraded anything from one major version of ASP.NET MVC to another. Is that a better situation?