Personal Experience: Part 2 – Tails

3 minute read

Posted by: Joseph Meehan October 6, 2014

This a post in series of posts describing a personal experience from learning about the DNM’s to becoming a vendor – all the parts of this series will be available to here: ExperienceTag

Part 2:

Privacy and security are important to people using Darknet marketplaces. The ability to purchase and vend goods and services without being spied upon is one of the main tenements of these marketplaces. TAILS is an operating system that is tailored to these needs. The name stands for The Amnesiac Incognito Live System. TAILS is widely accepted as the leading live operating system in built-in privacy and security features. More information, downloads and documentation can be found at

Downloading TAILS was easy enough, but I ran into some trouble verifying the download. The TAILS developers used PGP keys to crytographically sign the download so it could later be verified using their public PGP key. Using the terminal I was able to eventually verify the CD image, but it was a bit of a mission. I had to download the CD image three times before I got a good one. Once it was verified I used Universal USB Installer to burn the .iso file to a thumbdrive. From there all I had to do was boot from the thumbdrive at startup and I was ready to go.

Once I had TAILS up and running I was greeted with a pretty standard desktop experience. I’m familiar with Linux operating systems and the various desktop environments available (Gnome, Cinnamon, KDE), so adjusting to TAILS’ desktop environment was relatively easy. It reminded me the most of the XFCE desktop environment. Toolbars and an application menu at the top, window list at the bottom and time and date and session options in the top right corner. An Email client, browser, file manager, instant messenger and other common programs all come preconfigured to take advantage of the privacy and security features in TAILS. The OS documentation is placed on the desktop for easy access. Many questions a first-time user may have can be answered by a quick perusal of the documentation. As soon as I connected to an internet connection TAILS automatically started the TOR anonymous internet service and notified me when ready to connect anonymously to the Internet and Darknet. It can take some time for the TOR service to start, and there is no readily available way to see any progress. So be patient, you have to wait for the TOR icon to appear in the toolbar.

Now that I had TAILS up and running I was unsure of exactly where to go. My friend Grandi had pointed me toward a Darknet search engine called Grams. I searched for it using the default search engine in Iceweasel (TAILS TOR browser) and realized as I clicked on the link that Grams was the first Darknet .onion website I had ever been to. I felt like my journey was really getting started at this point. I noticed on the TOR network that sites can take longer to load than through a standard Internet connection, so again be patient if it seems like your connection is slow. Grams was really easy to use and provided a lot of information in the search results. I searched around a little bit using some terms related to what I want to offer on the Darknet. There weren’t many entries about freelance writing. I only came up with about four results when I searched for ‘freelance writing” and none of them were actual writing services. The same results were returned for “freelance writer.” There was definitely a gap on the Darknet for freelance writing services, but the real question was whether or not there was demand.

Now that I have TAILS up and running as a good start to maintaining my privacy on the Darknet, it was time to learn to use PGP keys to encrypt my e-mail communication.

Updated: 2014-10-06