Ruminations on the Digital Realm

Jan Stedehouder

Portable Security for the Practical Paranoid

Recently I have been thinking about my online security. A bit late, some might say. True and I still don’t have to worry too much. On the other hand, I am getting more concerned that under the banner of “we have to stop the bad guys” all of us have to give up part of our civil liberties. If we continue on our current tracks we may reach a point that Orwell’s 1984 can be considered an utopian vision.

Anyway, it lead me on a brief search for portable applications which at least give me the feeling that I am more secure that I am now. The first step was to make my e-mail traffic more secure and make it more difficult for all kind of snoopers to read in on my e-mail. There is great portable version of Thunderbird, which can easily be extended with GPG encryption. It is simply a matter of installing the GPG for Thunderbird extension and then Enigmail to encrypt and sign your outgoing traffic. Of course you need to have a strong passphrase, but once that is done, it is no longer a problem to send (and receive) encrypted e-mail messages that would give various governments some headaches.

The second step was to obscure my going arounds in the digital realm. Could I obscure the digital crumbs that I leave behind while surfing the net? The answer, of course, is yes. There is a portable version of TOR. The package consists of Tor, Privoxy and Vidalia and the combination makes it very easy to hook up to the Tor network and obscure your own IP address. No doubt you will use Portable Firefox along with it, so the developers of Portable Tor suggest you use the Tor button extension for Firefox to enable/disable Tor from within the browser.

With e-mail and webbrowsing more secure, I want to make sure that no one could just plugin my USB drive and access those portable applications. I needed more security and that was provided by Truecrypt. Truecrypt is open source (I forgot to mention that, but that was the main requirement) and it allows you to encrypt a complete USB stick/drive or create an encrypted drive on a stick/disk. In the latter case Truecrypt will be installed as well in traveller mode. The online documentation is solid. The program is multiplatform though the Linux version is commandline only.

I created a new file, which became the encrypted container for a 1 Gb “drive”. You really have to be patient, because it took about 30 minutes to set it up. Now I have a USB drive that autostarts Truecrypt and asks for the password. You can also use GPG keys again, but you need to keep those at hand as well. Truecrypt then mounts the new drive and that gives me access to the secured versions of Thunderbird and Firefox.

The weakest point in the chain are the passphrases, which are stored in my head. So, any not so scrupulous police force that considers “please no, not again” as enough civil liberty, could try to beat it out of me. So there is a serious need to add another layer of portable security to the system. And I think I found it.

SumoWrestler This is a completely portable layer of security with enough substance to pack some punches.

If you have some more suggestions to increase the portable security for the practical paranoid, feel free to add them.


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