I recently upgraded from 1.11 to 2.2 in one go. I didn't have any issue at all, besides a problem with mysql drivers. I had to switch from using PyMySQL, which

I recently upgraded from 1.11 to 2.2 in one go. I didn't have any issue at all, besides a problem with mysql drivers. I had to switch from using PyMySQL, which is not the one recommended by Django anyway, to mysqlclient, and that caused one minor problem that was trivial to fix. Looking at the release notes for 3.0, I'd expect that if I migrated from 1.11 directly to 3.0 it would've been a smooth transition. Of course it depends on your codebase. In the past I worked on a project which interacted a lot with Django internals, with a lot of code reflection involved. Upgrading that was a pain even between minor releases.