Shortcut Messed Up Path + Tor Connection

Hello. So, although I have been using Whonix on Virtualbox for a little over a year now, I should still be considered a beginner user, because I really only use it in a simple way without messing around with any settings or advanced features.

Unfortunately, recently I have been experiencing issues with Tor connection, which of course means the workstation is not getting internet. So, what I did was install Whonix on a new device, and I found out Whonix is now the Lxqt version, and I was using the older Xfce version on my main device. Anyway, on my other device the new Whonix is connecting and working perfectly. However, on my main device it is still having troubles, although it works for a few seconds at a time and is still able to load pages.

So, my main problem is that I have a signed-in app on my Whonix workstation which is preventing me from just reinstalling a new version of Whonix, because the app is only signed-in on Whonix and can’t be accessed without that exact session. Although it may be possible to just swap the gateway, my plan was to get the login code when the Tor connection is up, then once I have my accounts safe on another device, I can try reinstalling. Because of course I don’t want to make anything worse trying to fix the connection like I already did.

So, the really bad thing is while I was trying to fix it, I decided to open the app from the main menu list called “All Applications” which I have never used to open the app before because I always used my desktop shortcut to open it. I’m not sure why but what happened is that it opened the app as if it was just installed and it is showing me the sign-in page like it’s a brand new app and not remembering my session. The very problematic thing is that opening it from that menu seems to have messed with the shortcut pathway. Meaning, that now the desktop shortcut I always clicked to open it is now also opening the app like it is a brand new session and not remembering my sign-in accounts and data.

(Very Important Note) - At one point I believe I duplicated this specific app which is a potential cause for this. Also, the app is actually displaying twice on the “All Applications” list, but both versions are now both opening the brand new session version without my signed-in account and data. However, the good thing is that I never signed-out of this app and all the data is still there, and I am praying this is an easy fix.

I would truly appreciate help resolving this, and please explain steps as if I am a very beginner user. Thank you.

It’s a bit tricky to know what to do unless we know what app it is. This is very likely unspecific to Whonix, so if you would rather not disclose which app it is, I’d recommend looking for that particular app’s official support forums / chatrooms / whatever they have, and asking this same question there.

As for Tor connectivity being broken, Whonix 17 (the last version to use XFCE) has been out of support and has known security vulnerabilities in it, so upgrading to newer versions as they become available is highly recommended. As for why Tor isn’t working for more than a few seconds at a time, that sounds primarily like a Tor problem, potentially caused by your version of Tor being outdated. You might be able to install a newer version of Tor from the Tor Project in the gateway to resolve the issue, but you should use VirtualBox’s snapshot feature to create a snapshot of the gateway before trying this in case it makes things worse.

The app is Telegram. I think the issue is perhaps specific to Whonix because the same thing would likely happen after duplicating any app in Whonix, and I think it has to do with fixing the shortcut path and determining where the original folder with the app data is and how to open the app version that’s signed in. Which is more complicated for me since it is Whonix.

For Tor, I realized that it was an old version, but only after seeing there was a new version on the website. This is not neccessarily the main problem, but I can try to fix it by getting a new Tor version. What happens if I install the newest Whonix version lxqt gateway. Will the new Whonix lxqt gateway provide a Tor internet connection to the outdated xfce workstation I have if I run them together.

Can you clarify what you mean by “duplicating an app”? What exactly did you do to result in the app being installed twice, or end up with two copies of it otherwise present on the system?

I believe that will work, yes.

So, I believe I was trying to bypass the accounts per device limit of 4, which I resolved soon after by downloading Ayugram the custom Telegram client which serves as a second app to store the rest. However, before that I believe I cloned the app by following a guide which included: Right Click on App → Opening File Location → Then Copy and Paste the Folder and rename it to Telegram2. But, I never used it like this because the other method was much better.

Also, will importing a updated Whonix appliance change the old ones? Basically, can you have 2 Whonix appliances on the same Virtualbox? I was going to try this on my other device to not mess up anything on my main device, but again this is not my main problem as I believe Tor works long enough at a time to recieve my login codes.

Whonix does not adjust Telegram’s behavior in any way, so how it behaves and how to fix this situation depends entirely on how it works. Whonix developers aren’t familiar with Telegram’s internals, so we can’t be of much help. The only meaningful advice I can give here is to snapshot the Whonix-Workstation VM before doing anything else to attempt to recover the session, so that if it does still exist but you do something that destroys it entirely, you can get it back by restoring a snapshot.

A Telegram-specific support channel would be best for further help with this.

It will not, you will end up with new VMs created alongside the old ones, which I believe is what you want.