Nesting TOR within VPNs

Discussion in 'BlackHat Lounge' started by gmp123, Sep 5, 2015.

  1. gmp123

    gmp123 Newbie

    Jan 23, 2015
    Likes Received:
    I was reading somewhere about the differences between routing Tor through your VPN, and your VPN through Tor, the difference being who do you trust more, the Tor exit node, or the VPN, via these diagrams:
    [COLOR=#FFFFCC][FONT=Helvetica Neue]User---VPN---Tor--- destination site[/FONT][/COLOR]

    [COLOR=#FFFFCC][FONT=Helvetica Neue]User--- Tor---VPN---destination site[/FONT][/COLOR]

    Then there's this third diagram which I'm trying to figure out, which prevents Tor from knowing where you're from, and where you've been, which is the well known weakness with Tor.
    [COLOR=#FFFFCC][FONT=Helvetica Neue]User---VPN---Tor---VPN---destination site[/FONT][/COLOR]
    Of course with the third option, you still have the problem of the first VPN knowing your IP, but you eliminate the "tor exit node back tracing" thing that the VPN > Tor option has. Of course if you went this route of VPN > Tor > VPN you'd still have to worry about the VPN not keeping logs, payment methods, etc, but it seems like the best bet.

    I'm just wondering how it works. Would you connect to your VPN, then load up Tor, only to connect to the second VPN, so it sees the masked Tor IP? If that's how it works, seems pretty legit to me. What do you guys think? Is the added cost and layer of precaution worth it?