1. If I understand correctly, according to wiki, while using Whonix (—>Tor) —> VPN —> Firefox I at least won't leak my external non-Tor IP and DNS? That's not outdated?
Yes. Up to date.
2. If my VPN provider keeps logs, The IPs they'll keep still will be the Tor exit nodes, correct?
3. Also, wiki mentions that I can use Proxy/VPN/SSH -> Tor Browser -> website. Do you know where I can find information on how to do that? (i.e. how can I use Tor Browser with VPN IP?) When I simply enable VPN on Whonix-Workstation and use Tor Browser, it still has Tor IP.
"If you want to do it with Tor Browser, read Change/Remove Proxy Settings. "
3.1. Will I share Fingerprints with other Tor Browser users in this case?
Unfortunately, not exactly.
From https://www.whonix.org/wiki/Tor_Browser#Local_Connections (seemingly unrelated), but the information on transparent proxying applies here. See
"Note, accessing 127.0.0.1 using Tor Browser is no longer possible due to a change in Tor Browser by The Tor Project. You could set to transparent torification, but then you would be vulnerable to fingerprinting issues. See Tor Browser, Local Connections for more information and a workaround."
on that link (contains links).
4. After enabling SecurityKiss VPN according to instruction (https://www.whonix.org/wiki/TestVPN), I’m getting this message in Whonix-Workstation: «TransPort Test result: looks like you're not connected through Tor. Possible reasons: You added a VPN»
Does it mean that my connection is Host —>Tor —>VPN or I am literally not connected through Tor (Host —>VPN)? Is this something to be worried about?
Nothing to worry. If you're using Whonix-Workstation we're reasonably sure that all connections always go through Tor first.
Thank you and sorry if these are dumb bikeshedding questions.
They're not bad questions. Frequently asked questions. It's due to our documentation on that topic being bad. Ticket:
Most confusing comes from Tor Browser being configured to use a SocksPort by default (for https://www.whonix.org/wiki/Stream_Isolation) vs needing to remove these proxy settings (https://www.whonix.org/wiki/Tor_Browser#Change.2FRemove_Proxy_Settings) so system default (TransPort), VPN is being used by Tor Browser.