[Caligatio]

I'm super confused: doesn't Debian also have a 5 year support cycle? How is Debian better than Ubuntu on this particular issue?

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.

[metadat]

The Debian upgrade process actually works.

[Caligatio]

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.

[metadat]

"Maybe" is a major understatement on the Ubuntu upgrade fail front, friend.