virtualbox workstation and gateway weird behavior?

Hey my dudes,

I have an issue I believe with whonix’s inner workings.

I installed whonix with VB (used the new whoix debian installer script). I accepted the terms and Agreements in the workstation first so it was showing that it is looking for a tor connection (a progress bar). it failed multiple times, as my Gateway was not running, since I accpeted the terms later. And when I did that, in the middle of the progress bar in the workstation (connecting tor or smth like that was the header), it was finished and successul, even though it had like 300s …

(Moreover when I ran upgrade-nonroot in both boxes it always said bookworm, but my host is debian bullseye… Or is this because whonix is based on bookworm and that is what the upgrade-nonroot logs were referencing…)

So THE QUESTION: I am worried that not setting up the gateway first on initial install, it fucked with my whonix workstation. And I am not sure if some configs or settings are now messed up. Is it recommended to remove them from VB and import them manually?

Yes, and you should upgrade your host to debian stable which is bookworm atm.

Just turn off WS and GW, then start GW first then wait for 0.5 minute then run WS and check if the connection established.

Something tells me you are from Germany for correcting that typo in my post XD

Anyways, thanks. So What if I dont upgrade to bookworm? because they have a lot of non free softwaqre… And If I saw right in the auto installer script, it was not only for bookform but any distro… So that initial accpepting of agreements which led to workstaion being initially set up without gateway set up, is not an issue and is handled internally? Or should I remove and import them to virtualbox manually this time

You will have the oldstable version of Debian, which might still contain missing features or bugs that are already fixed in Bookworm.

Debian doesn’t enforce (yet) installing nonfree packages by default (afaik).

No issue.

5 posts were split to a new topic: SSH IP Leak Testing

Hm, but then I would have to remove everything right? And then run the installer script again?

Upgrading between Debian versions doesn’t require removing everything; you just need to change the repositories and perform the upgrade.

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Nope, not that i know.