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I am new here and have a question about using Tor as an anonymous middlebox.

I have a Windows machine and I want to anonymise my internet useage from time to time. The Tor browser is a fantastic application for basic web browsing, however as soon as you watch a Flash video, run an application outside of the broswer you're screwed.

I have a spare Dell box with two NICS, if I install Ubuntu server on it, install Tor and configure it correctly to listen on both NICS, and use this computer as a gateway server for my Windows box, can I stop things like flash from giving away my real external IP address? I'll configure the Ubuntu server's NIC's on two different networks. One that is on the same network as my router and one that will be on another network that my Windows Box will be on.

In a nutshell what I want to do is get all my network traffic from my Windows box going through Tor.

Who thinks this will work lol?

Any opinions would be greatly appreciated!

  • You might want to check out Tails: tails.boum.org – user194 Jun 8 '14 at 0:41
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    Perhaps it would be, perhaps it wouldn't, I appreciate your opinion, however I would still like to give it a try :) What do you think the difficulties would be and what are the caveats of doing it with a standalone Windows box and a linux proxy? Why would there necessarily be security holes pushing all traffic from Windows through a Linux box running TOR? Really interested in your opinion on what these security holes are. I am on here to learn just as much as to 'do'. Thanks again! – user2933 Jun 8 '14 at 20:22
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    For the Linux Tor proxy, proper routing and iptables setup is the hardest part. But there are various guides, and you could see how the Whonix gateway does it. For the Windows box, configuring apps to use Tor properly is the hard part. The browser is easy using TBB, but you need to disable the local Tor process. That's also documented by Whonix. But you can't trust Windows. You don't know what it leaks to Microsoft etc or how. Some stuff going out is encrypted -- to "protect you", of course ;) And do you really want to be using Tor on a box with a money trail back to your true name? – mirimir Jun 9 '14 at 4:29
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    You probably can setup a configuration where all of your traffic is routed through tor. But do you really want that for all the traffic? The next problem is that within you traffic there might be a lot of information that can be traced back to you. Cookies, browser plugins, your dropbox account,.. Using Tor to read your GMail does not help. Google will still know that it is you,.. And there might more of these identity giving things on your PC than you are aware off. – Lars Pötter Nov 5 '14 at 23:08
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No insult intended, but that would be an ambitious project for someone asking a question like this ;) I recommend starting with Whonix. Whonix comprises two virtual machines (VMs). One is a Tor gateway aka "middlebox" and the other is a workstation. Both are Debian. The workstation includes the standard Tor browser and many other apps that are configured to use Tor.

Installing Whonix is very easy. After installing VirtualBox in Windows, you just import the two Whonix appliances (VMs). You start the gateway VM, complete the setup dialog, and then use the workstation VM. That's it :) I gather that it's possible to install the Whonix gateway and workstation on "bare metal" rather than as VMs. But I've never done that.

I don't recommend using a Tor middlebox with a Windows box. It would be a waste of time, given the potential security holes. However, if you're determined to use Windows, I recommend using one of these Windows 7 VMs in VirtualBox on a Debian host. Just be sure to download it using TBB, and never run it except via the Tor middlebox.

  • Is Whonix a full Debian? I've avoided it mostly because KDE sucks. If I can run Gnome 3 shell then I'm there. :) – Jeff Burdges Apr 20 '15 at 5:07

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