You will need to pay attention to
https://github.com/collectiveidea/delayed_job#upgrading-from-2x-to-300-on-active-record when you bump up to 3.0. DJ has long been pretty conservative in our version requirements, so you will end up upgrading DJ in stages along with rails. The biggest change that doesn't really have a migration path is the YAML handling between ruby versions. You will reach a point where old and new jobs simply can't read/write each other's formats. My guess would be that someone somewhere has written a migrator, but I have never used one nor am I sure where to find one. I don't remember off the top of my head when that YAML change happened. Also if you use any of the gems that hook into DJ internals, things have change a lot there, it is 8 years worth of development. Also, the ActiveRecord adapter is really the only one actively supported at the moment that I am aware of.