I upgraded two squeeze and one lenny this month. It went rather smooth; lot of config-fixing though. #Debian handled library deps just lovely.

Now #Debian upgrades I'm not afraid of. Those go smooth far more often than not. (Though... lenny? Jeez, that's ancient!)

It's just that I'm running stuff like postgres 9.6, and the last time I tried upgrading (dumpall -> upgrade -> restore), everything broke, error messages were completely unhelpful, and I ran out of time. So I'm back at 9.6, and feel a little bad about that.

Guess I'll try again a year or two from now. :P

I have two kinds of pg upgrade: for small db I just let `pg_upgradecluster` to do it and so far no trouble. For big ones I use `pg_upgrade ... --link ...` and have backups ready [no trouble so far 9->13]. 😛

Hmm, hmm. I should try that. Maybe I will, I do have a couple of very small DBs to test it on.

Thanks!