This server has been running Debian for the past 5 years, starting with Debian 8. I’ve continually bumped the version number along the way.
I just upgraded from Buster (10) to Bullseye (11) and the only pain point was going from Ruby 2.5 to 2.7 (Bundler depended on 2.5). Quick fix though!
Can’t wait to get another 5 years out of this thing.