Home » Jolly Roger’s Security Guide for Beginners » HOW TO CONNECT TO TOR OVER TOP OF TOR
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Here is another fun tip that may or may not interest you, but I figured I would throw it in for you anyways.

>>>Attention: Use VPN with Tor! Click here to see the best VPN’s<<<

I figured this out while trying to figure out an effective way to do a TOR -> VPN connection. You can do TOR -> TOR connection with Tails by using a program called Tortilla, thus adding another layer for your adversaries to crack. Whether or not this is worth it, is completely up to you, but I am sharing in case it is something you want to do. This however currently only works for those using Windows because it was designed to be used by Windows users. Please note as well that this will noticeably slow down your connection since you are going through TOR twice. Here is the official homepage of Tortilla.


And the official download page for the prebuilt standalone exe below. There is a link to it on the home page if you do not trust me.


The way you do this is very simple actually. You need to first download TOR Expert Bundle from the TOR Project download page and install it on your computer or better yet your USB drive.


Next open the tor.exe and just let it run until it says Bootstrapped 100% Done. Next you want to run the tortilla.exe file and make sure you run it with Administrator privileges. Also, if you are running Windows Vista or later, you will likely get an error that this program does not have a valid certificate, because it is actually signed with something called a test-signed ceritifcate. In this case you need to allow test-signed drivers to run on your computer.

To do this, simply go to your Start Menu and type in the search box “command”. When command comes up, you right click it, and click run as Administrator and it will open up a command prompt. Next type in the following command. Bcdedit.exe -set TESTSIGNING ON and this will allow Windows to install test-signed drivers. Restart your computer and you will see in the bottom right hand corner after you restart Test Mode Windows. Now you can run Tortilla. And let it connect to TOR. Remember to have tor.exe from TOR Expert Bundle open first.

Finally, you open up Virtual Box or whatever Virtual Machine software you are using and click Settings on the Tails virtual machine. Click on the Network tab and change the drop down menu where it says Attached To: to Bridged Adapter and in the drop down menu below it called Name: Select Tortilla Adapter. Now your Virtual Machine, in this case Tails, will always connect to the internet through Tortilla, which connects through TOR. And since Tails establishes its own connection to TOR, you will be running TOR over top of TOR. Again, you may or may not want to do this, but I am giving you the option should you want to.

If anyone is interested in learning more about the creator of Tortilla, he did a PowerPoint presentation at the 2013 Black Hat USA conference. Feel free to watch his talk at the YouTube link below. Please note however that YouTube is owned by Google and there are only about 57 views on the video, so the government will likely correlate users who watch that video with users from this forum. Make sure you do not watch the video on YouTube with your real IP address. At the very least use a VPN or find another site that has it hosted. Always be extra paranoid.


  1. “Make sure you do not watch the video on YouTube with your real IP address. At the very least use a VPN or find another site that has it hosted. Always be extra paranoid.”

    Too late now you’ve embedded the fucking flash video!

  2. If it was not blocked already, then your browser is misconfigured tbh.

    Suggestion – noscript settings within TBB



  4. Hmmmm, downloaded Tor Expert bundle but it does not install !
    Tor runs always hidden, no window opened !Can´t install tortilla adapter, tryed many install instructions even this doesn´t work too for me :((

  5. Tor over TOR is very simple task. HOW?
    1.Run real Windows-1 and over it run VMWare or another virtual WinOS-2.
    2.Install proxy soft like CCProxy on Win-1 and setup to use proxy chain with IP=localhost:9150 <-this is default TOR-1 port. This is needed because Tor block external connection.
    But any Socks5 proxy/forward tool will do the same thing.
    3.Run newer Tor Bundle-1 on Win1 and separated TOR-2 on Win-2
    4.Go to TOR-2 config file torrc or TOR-2 network settings and check TOR-2 to use proxy and set up this proxy IP to be LAN IP of Win1 and CCProxy input socks5 port 1080.
    5.Run your favorite browser on Win-2 and set to use a socks proxy on port 9150 (this is local TOR-2 in port) or just use TOR FFox default browser with java off is the best.
    6.Enjoy TOR-2 over TOR-1 stealth connection and don't forget to delete every private data before every new TOR session in your favorite browser.
    7.Good practice is to use fresh installed clean system + Faronic DeepFreeze 8(protect HDD+bootsector) and run every tor in sandboxie, use CCleaner with max options before install of DeepFreeze and sandboxie. Del frequently your sandboxie or restart your freezed system after every final session with sensitive WWW.
    8. Be good

  6. Have you ever thought about running your phone as a tor router for a broadband connection? Also, running tor along side a vpn in windows. You can host this way, as well. All with a few simple configurations. Also not to mention, if you use a tor router you don’t have to use software, or configure your browser.

  7. A nice and easy alternative is to use I2P with Opera instead of TOR. With the built in unlimited free VPN you dont have to do any extra configuring etc. Granted I2P can be a pig to set up for the first time

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