I 'inherited' a largely outdated system based on Debian 8 (virtual private server hosting environment). It's pretty natural to go and upgrade to Buster.

But I wonder if upgrading from 8 to 10 is possible (directly)? Is it even safe? What would be the best way? Should I go via 9 (so edit sources.list to have oldstable repositories first since 9 is now old stable?)

I would probably scrap/reinstall but there is a catch: it has apps running (and some Python 2 scripts probably need to be ported to 3...), outdated node and other apps so I may only hope that custom-installed things working on older node will keep working on new node.

  • There's relatively minimal benefit to upgrading the operating system if the stack you're running on top is left untouched. Better to do the scrap/reinstall as you describe and put the effort into upgrading the runtimes as well.
    – gary
    Commented Oct 16, 2019 at 18:28
  • 1
    8 to 9 to 10 or build a new 10 system and migrate the services and data from the 8 system over are your options. As user gary points out if your stack is working and the risks are mitigated why do you need to upgrade? Python 2 is not support in Debian 10 is one issue but there may be many issues. These are problems system administrators are paid to deal with so this is a very open ended question as it stands. Could you edit it to be about a more specific issue you are facing? Like getting a specific application from Debian 8 working on 10 or an issue with the upgrade process itself? Thank you.
    – kemotep
    Commented Oct 16, 2019 at 18:35
  • Python/etc should be relatively easy to port in my view. The thing is "will it work" (the OS) after upgrade. I'm now considering to create a backup VPS, making an upgrade (apt-get), working on changes and checking if it works. If it does not, I need to reinstall. But I must upgrade because Debian 8 is no longer supported in 2021. Some stack I run demands an upgrade too (because it needs a new Node). So I have to upgrade some of the stack too
    – fggor
    Commented Oct 17, 2019 at 7:06
  • It's funny because I now see that release notes from debian 9 recommend doing "upgrade", "dist-upgrade", and install of latest kernel separately and prior to first reboot. I wonder if not installing latest kernel would keep the system working?
    – fggor
    Commented Oct 17, 2019 at 7:32
  • @fggor that depends on what version of the kernel is currently running. A current Debian 8 kernel should be sufficient to run Debian 10. Commented Oct 17, 2019 at 7:34

1 Answer 1


When upgrading, you shouldn’t skip releases.

However, in your situation I would recommend setting Debian 10 up on a new VPS, copying your scripts etc. across, checking that everything still works, and only once it does, decommissioning the old VPS.

  • Thanks, though I still wonder if trying dist-upgrade first might work. In principle assuming I've got backup of everything I could try this first... I don't have an option of having a spare VPS.
    – fggor
    Commented Oct 17, 2019 at 8:01
  • Yes, it might work; if you have backups then you should be OK either way ;-). Commented Oct 17, 2019 at 8:11

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