this post was submitted on 13 Dec 2024
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FWIW I've got a Debian server that hosts most of my sites and primary DNS server, that's been running since Etch (4.0, 2007ish). I've upgraded it over the years, switched from a dedicated server to OpenVZ to KVM, and it's still running today on Bookworm. No major issues with upgrades.
It's definitely not something that will happen 100%. I've also had long standing debian systems that seem to not care. However I've had plenty that, for whatever reason couldn't handle multiple major version hops and just eviscerated themselves, I've not had that with arch personally. You may need to download the latest statically built pacman depending on how old it is but that and a keyring update usually has you covered
Debian only supports upgrading one major version at a time. If you're upgrading from Debian 10 to 12, you need to first do 10 to 11, then 11 to 12. Upgrading multiple versions at a time is completely untested and unsupported.