Need some help with Tails

Discussion in 'privacy technology' started by WhoIsTylerDurden, May 13, 2016.

  1. WhoIsTylerDurden

    WhoIsTylerDurden Registered Member

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    okay so i have tails installed on live usb.

    I have everything all set up and ready to go as far as encrypted email, pgp encryption, bitcoins in my electrum wallet.

    Now my problem is getting a vpn on there. I dont know if its possible or what. I read on tails boum that it wasnt intended to have a vpn used with it. Which i think is stupid. Why have such a secure OS with no way to encrypt your traffic?

    I tried installing openvpn through terminal amd of course couldn't. Any help would be appreciated guys. Thanks im a noob haha
     
  2. mirimir

    mirimir Registered Member

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    Well, Tails is built to use Tor, not VPNs. And Tails is a LiveCD, so you can't really install stuff. You can install stuff if there's enough ramdisk, but it'll be gone after reboot. To add a VPN client, you'd need to build a custom Tails LiveCD. And that's nontrivial :(
     
  3. WhoIsTylerDurden

    WhoIsTylerDurden Registered Member

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    So would i be better off not using tails if i wanted to be more anonymous ?

    My plan was to use a vpn -> tor -> internet.

    I guess what would you recommend mirimir? Or what setup do you use. Im all ears.

    Been studying this stuff for a solid 2 weeks and the whole being almost anonymous on the internet really intrigues me
     
  4. mirimir

    mirimir Registered Member

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    I use Whonix through nested VPN chains. There are guides on IVPN about that, linked in my sig.
     
  5. WhoIsTylerDurden

    WhoIsTylerDurden Registered Member

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    Awesome thanks!

    i want to further my knowledge on the subject, is this the forum to be at or are there others with more specific intentions towards these softwares? (Tails, whonix)
     
  6. mirimir

    mirimir Registered Member

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  7. WhoIsTylerDurden

    WhoIsTylerDurden Registered Member

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    Hey i'm back haha.

    so i went and read through your article on IVPN for the basic install. Now i have a few questions.

    I have a laptop that is completely wiped of data connected to me. i do have kali linux 2.0 running on the hdd though and i love using it for Pen tesing and what not.

    my question is can i install VirtualBox on Kali and then run 2 vm instances of Whonix and Whonix Gateway? through nested vpn's?

    heres a vid i saw kind of correlating to what im talking about except i would be running 2 Whonix vm's on Kali OS. if that doesn't make any sense feel free to call me a idiot haha. im learning though!

    https://www.youtube.com/watch?v=_ZRHJvq4C40
     
  8. mirimir

    mirimir Registered Member

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    Sure, Kali is just Debian plus stuff. It is better to use a dedicated host, but you have what you have. I'd hit Tor through at least two chained VPNs. One VPN can be on the host, so you'll need one pfSense VM and two Whonix instances. The pfSense VM needs 0.4-0.5GB RAM. Each Whonix instance needs 1.0-1.5GB, ~250MB for the Tor gateway and 0.8-1.2GB for the workstation.
     
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