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Is it useful to run the Whonix gateway in a VM inside of tails, running as a liveboot, to connect to another VM like for example Kali, which also runs inside of Tails, because it would rout my traffic through tor 2 times and I still could setup a VPN in Kali so I would not face the disadvantage of blacklisted exit nodes or are there any other possible issues I do not recognize? Because I have read it would be kinda dangerous to use Tor over Tor but no one was able to exactly explain why. Thanks for any help or explanations

Warlord456
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    https://www.whonix.org/wiki/DoNot#Prevent_Tor_over_Tor_Scenarios – adrelanos Jul 13 '19 at 16:56
  • Ok I understand that it's easier to identify someone who uses more than 3 hopes in a row but what if I add another VPN so the setup would be Tor>VPN>Tor>VPN nobody (except the provider of the first VPN) would notice that my traffic is routed through 2 times am I right? And I still don't exactly understand why it's possible dangerous to get the same node 2 times – Warlord456 Jul 13 '19 at 18:12
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    related: https://www.whonix.org/wiki/Warning#Confirmation_Attacks - It might result in using the same Tor relay as both Tor entry guard and Tor exit relay. Path selection is best left to Tor - unless being more clever than Tor. On VPNs see also: https://www.whonix.org/wiki/Tunnels/Introduction – adrelanos Jul 19 '19 at 12:48
  • Tor-over-Tor should always be avoided: https://tor.stackexchange.com/a/11922/5234 || 2) a VPN has nothing to do with anonymity: https://tor.stackexchange.com/a/20033/5234
    • – DJCrashdummy Sep 01 '19 at 11:52