in-place upgrades possible? If (not) so, why? Recommended? ( Whonix 12 -> Whonix 13 )

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#1

Also wanted to add, hugely thrilled to see that Whonix 12 -> 13 upgrade will be possible in place if desired, without restarting from scratch and a fresh installation. For some that latter option may be fine, but for someone like me who installs A LOT of software on Workstation, the prospect of starting over and redoing it every time, is horrible.

Is that update method only possible this time because Debian 8 Jessie is still the base version for Whonix 13? Meaning when a Whonix version based on Debian 9 Stretch is released, we will still at that point have to do a totally fresh install? Or will an in-place upgrade path always try to be provided?

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Whonix Update Failure - Recieved HTTP code 403 from proxy after CONNECT
#2

Completely understand your point of view - especially since I like to tweak settings until everything is exactly how i want it. However, I force myself to do a fresh install with every major release. It’s much less painful to do with Linux (and even less with Qubes) than you might think since most (if not all) of your customizations will be in /rw. Also, you can wait until both Qubes & Whonix have major releases ready.

Some reasons why I always do a fresh install:

  1. In-place upgrades have much more variability than fresh installs and thus, are much more difficult to test as thoroughly. For security distributions, you don’t want to be the experiment.
  2. Hopefully, I’ve learned something since the last major release and will be that much smarter configuring the new system.
  3. Lots of software installs might mean accumulated crud. And software you no longer need.
  4. You can never get enough practice with backing up and restoring.
  5. (EDIT) Knowing that you’ll be performing fresh installs regularly keeps you more disciplined - to take notes, and to avoid unnecessary changes to TemplateVMs.
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#3

Whonix 12 → 13 in-place upgrades (using apt-get) will very most likely be possible.

Instructions are testers-only at the moment and can be found here:
Release Upgrade - Whonix

(While simple apt-get dist-upgrade does not result in something to explode, these wiki instructions are better than just apt-get dist-upgrade because then more cruft will be removed.)

Last time in-place upgrades were not possible was during Debian testing → Debian stable transition. A base distribution (Debian) downgrade was not sanely possible given the resources at hand.

Whenever resources are sufficient to allow in-place upgrades, it will be made possible.