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I have a VPS (Linode) currently running Debian Jessie 8.10 for my personal website. Every few years I need to upgrade the Linux major version. Since a new major version usually means my many package config modifications are overwritten, become incompatible and/or need to be merged with the updated config files, this has always been a somewhat painful exercise.

How can I upgrade with the less hassle and downtime due to broken config files?

For the sake of argument, let's pretend I know which config files I've modified.

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    You obviously do some testing first. Be very wary about upgrading from 8 to 9, it can break PHP scripts and MySQL badly.
    – Rui F Ribeiro
    Apr 27, 2018 at 22:09
  • I'd imagine it's possible but I don't know how you might get a config diff. Personally, I install etckeeper with all fresh OS installations. It's a great way to keep track of configuration changes. One of these days, I'll get around to learning how to use Ansible or some other configuration manager.
    – Anthony Geoghegan
    Apr 28, 2018 at 16:50
  • @RuiFRibeiro have edited question to make it less broad, can it be re-opened?
    – dbdemon
    Apr 30, 2018 at 9:57
  • @dbdemon I am afraid it is still too broad. The upgrade from Debian 8 to Debian 9 is traumatic even for experienced users. I would center on specific questions and packages. Unfortunately, there are not silver bullets. I do not feel compelled to vote to reopen this as it is, someone might have a different opinion.
    – Rui F Ribeiro
    Apr 30, 2018 at 18:20

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I take major version upgrades as an opportunity to rebuild and reconfigure, test my backup and restore process, etc. on my Linodes. Sure, it costs me an extra $5 if I take my sweet time about doing it (or $1 if I hurry... not worth it).

As far as finding your changed configs, the editor I use (joe) is set to make a backup file of any file edited wiht the same name ending in a tilde (~). So find /etc -iname *~ works for me ...

That said, take backups of EVERYTHING, perhaps even a snapshot. Read the Debian docs on doing an upgrade. Check changes in core things that can break other stuff - as Rui F Ribeiro's comment says, the PHP change will break things and possibly the mysql->mariadb transition too. Check your various web apps, services, etc. to see if they will be affected by any of these changes (ie, in PHP the mysql_* function family is gone - change to using the mysqli_ family or PDO).

Finally, once you are ready, proceed with the upgrade. It will hopefully be as painless as changing the sources.list and doing an apt-get update && apt-get dist-upgrade.

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