Silk Road Author Arrested Due to Bad Operational Security

Details of how the FBI found the administrator of Silk Road, a popular black market e-commerce site.

Despite the elaborate technical underpinnings, however, the complaint portrays Ulbricht as a drug lord who made rookie mistakes. In an October 11, 2011 posting to a Bitcoin Talk forum, for instance, a user called "altoid" advertised he was looking for an "IT pro in the Bitcoin community" to work in a venture-backed startup. The post directed applicants to send responses to "rossulbricht at gmail dot com." It came about nine months after two previous posts -- also made by a user, "altoid," to shroomery.org and Bitcoin Talk -- were among the first to advertise a hidden Tor service that operated as a kind of "anonymous amazon.com." Both of the earlier posts referenced silkroad420.wordpress.com. If altoid's solicitation for a Bitcoin-conversant IT Pro wasn't enough to make Ulbricht a person of interest in the FBI's ongoing probe, other digital bread crumbs were sure to arouse agents' suspicions. The Google+ profile tied to the rossulbricht@gmail.com address included a list of favorite videos originating from mises.org, a website of the "Mises Institute." The site billed itself as the "world center of the Austrian School of economics" and contained a user profile for one Ross Ulbricht. Several Dread Pirate Roberts postings on Silk Road cited the "Austrian Economic theory" and the works of Mises Institute economists Ludwig von Mises and Murray Rothbard in providing the guiding principles for the illicit drug market.
The clues didn't stop there. In early March 2012 someone created an account on StackOverflow with the username Ross Ulbricht and the rossulbricht@gmail.com address, the criminal complaint alleged. On March 16 at 8:39 in the morning, the account was used to post a message titled "How can I connect to a Tor hidden service using curl in php?" Less than one minute later, the account was updated to change the user name from Ross Ulbricht to "frosty." Several weeks later, the account was again updated, this time to replace the Ulbricht gmail address with frosty@frosty.com. In July 2013, a forensic analysis of the hard drives used to run one of the Silk Road servers revealed a PHP script based on curl that contained code that was identical to that included in the Stack Overflow discussion, the complaint alleged.

We already know that it is next to impossible to maintain privacy and anonymity against a well-funded government adversary.