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Just started working with a Debian Jessie (8) in a production environnent. While presently deployed it is not seeing any heavy use yet. I was looking at the OS LTS page, and I was thinking about how convenient it would be to just upgrade it before is start seeing some more steady use in our environment and possibly making things more complicated with a later upgrade.

I was looking for a procedure to upgrade from Debian v.8 to v.10 but most documented procedures are sequential in order (e.g. 8 -> 9, or 9 -> 10).

My question: should I upgrade sequentially, or there is some proper documented way to skip a main version while upgrading?

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    Yes, you must upgrade it sequentially. It is not recommended to upgrade more than one release in one time.
    – mariaczi
    Sep 18, 2019 at 15:31
  • You can upgrade there is no technical limitations (but exceptions) but if you're not a high grade technician you will just fail. Update one version at a time.
    – francois P
    Sep 18, 2019 at 15:55
  • @francoisP there can be technical limitations, in some configurations.
    – Stephen Kitt
    Sep 18, 2019 at 15:56

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The only supported upgrade path is to upgrade one release at a time, i.e. Debian 8 to 9, then 9 to 10. Each release has its own release notes, with caveats which may or may not apply to you; it’s usually harder to deal with them all in one go over multiple releases...

There’s some amount of skip testing which goes on during a release’s development, but you’ll see there that there’s no automated jessie22buster suite. Package maintainers also try to preserve upgrade capabilities across two releases, but that’s a nice-to-have, not a requirement (for example, transitional packages are usually published in two releases, and conflicts are usually documented for at least two releases).

Of course, it could work; the major obstacle when upgrading is the adequacy of the old kernel, and the latest Debian 8 kernel is sufficient to deal with Debian 10. But I wouldn’t risk it, especially not on a production server. You’ll end up spending more time thinking about and researching the viability of skipping a release, than it would have taken to perform both upgrades back-to-back...

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  • Yes I understand and this make sense, especially in a production environment where 'hacking around' is definitely not an option.
    – marsisalie
    Sep 18, 2019 at 17:05

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