The Debian upgrade process actually works.
I'm guessing I've done 6 in-place upgrades over the last decade and have yet to have one fail.
It sounds like maybe you've had issues but the process does typically work.
It sounds like maybe you've had issues but the process does typically work.
I've been upgrading the same Ubuntu server across LTS releases since 14.04 - now on 22.04 - without any major issues. Spending 30 minutes every two years to upgrade major versions isn't that big of a lift.