Upgrading from Debian Buster redux

General
1

I posted before about the possibility of dist-upgrading from Buster and was advised against it. But I thought of another approach that could work. I have not had problems with non-pi-hole related dist-upgrades in the past so I was wondering if the following would be a viable strategy:

  1. Back up the pi-hole configuration (pihole -a -t or use web interface).
  2. Uninstall pi-hole (pihole uninstall).'
  3. Incrementally update distribution: i) edit /etc/apt/sources.list substituting bullseye for buster, ii) dist-upgrade, iii) reboot, iv) edit again substituting bookworm for bullseye, v) dist-upgrade, vi) reboot.
  4. Run pi-hole installation (curl -sSL https://install.pi-hole.net | bash).
  5. Restore configuration using web interface.

Thoughts?

2

Give it a whirl and see how it works for you.

You may not get the result you intend, and may end up having to reformat and flash a new OS. Results vary.

3

As has been said before, the results may vary. It will work in some systems, but fail in others.

It is usually much faster to do a fresh installation of Bookworm than the dual OS upgrade path.

Also, if your Buster OS is 32-bit, you will end up with a 32-bit operating system.

4

Well, I did it. It took a little bit of work to get the dist-upgrade to work (some incompatible packages that had to be uninstalled) but once I got it up to bookworm, everything worked fine!

Yes, a fresh install would be easier in a way but it's such a pain to do an install without a monitor. And overall, it wasn't bad and I didn't have to do a headless install.

5

You may find some hidden issues. There are a lot of changes between bookworm and buster. Does cat /etc/debian_version show the correct point release?

6

12.6. Everything is working swimmingly.

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7

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