Generally, it appears that Ross Ulbricht was applying his economic and techno-libertarian philosophy to real life. As his project grew, his security posture improved – too late. The most serious mistakes that Ross Ulbricht made were made during the period Jan 2011 - Oct 2011. A full timeline of the events in the indictment is as follows;
DPR / SilkRoad Timeline Of Events
What an awesome thread! You guys have a ton of great ideas. Has anyone seen Silk Road yet? It's kind of like an anonymous amazon.com. I don't think they have heroin on there, but they are selling other stuff. They basically use bitcoin and tor to broker anonymous transactions. It's at [REDACTED ONION V2 URL] Those not familiar with Tor can go to
silkroad420.wordpress.com for instructions on how to access the .onion site.
Let me know what you guys think
—Quote from: altoid on January 29, 2011
NOTE: This is an abridged version of a longer post pulling out the lessons learned from the Silk Road Complaint/indictment of 27th September 2013. This post will only list the OPSEC errors, rather than explore them in detail.
The OPSEC Failures
The fundamental error is poor compartmentation. Ross Ulbricht, the real person and the online persona (Google+, LinkedIn, etc), and the Dread Pirate Roberts persona share ideological views and geographic locations. There is contamination between the two personas. Most of these seem to be due to the organic evolution of the Silk Road venture, where early naive Ulbricht makes mistakes that later smarter DPR wouldn’t. Unfortunately, the later DPR is more ideologically extreme and consequently less savvy about mainstream society. Here are the 4 errors i will be briefly discussing;
1. Poor Compartmentation
3. Geographic Location
Contamination: seriously fatal links created between personas
The compartmentation failures are somewhat pervasive, in particular the ideological “Austrian School of Economics” and the mises.org site. However two particular contamination errors stand out:
1. Silk Road –> altoid –> rossulbricht@gmail . com link in 2011
2. Ross Ulbricht –> frosty@frosty . com –> Silk Road server link in 2013
The first of these failures happened because the altoid persona used to promoted Silk Road was poorly fleshed out (e.g. no email address). Ross did not put the plumbing in place to backstop his altoid cover. He then joined the BitcoinTalk community using this contaminated cover. His participation and search for social validation left him with his guard down. Consequently, he revealed a great deal of profiling information about his project and beliefs. Many of his posts are about Silk Road infrastructure or his mises.org influenced economic theories. After participating for 10 months he finally made the fatal OPSEC error of posting his personal email address.
The second error was poor compartmentation of his online Ross Ulbricht persona, the tech savvy San Francisco based startup guy, and “frosty” the system admin of the server hosting the Silk Road site. His poor compartmentation, likely using the same computer for both personal and business use, and his limited backstopping of the DPR/altoid/frosty persona meant that any error would be fatal.
These two errors combine to link Silk Road with Ross Ulbricht, and Ross Ulbricht with Silk Road.
“What do Ulbricht and DPR share?”
>> Profiling: Ross Ulbricht talks and acts like Dread Pirate Roberts
>> LinkedIn profile
>> Timezone leakage: private messages, forum posting times
>> BitcoinTalk altoid posts about: economics (mises.org), security, programming
>> Silk Road Forum Dread Pirate Roberts -> Mises + “Austrian School of Economics”
>> Mises.org Ross Ulbricht account
Ross Ulbricht, the person, was an active participant in the mises.org website and the BitcoinTalk forums. In both cases he was deeply committed to the “Austrian School of Economics”, something the Dread Pirate Roberts was also a huge fan of. The altoid cover alias, linked directly to Ross Ulbricht, frequently talked about bitcoin security and PHP programming. He is, based on his posts, clearly involved in running some sort of PHP based bitcoin using venture that requires high security. Sort of like the Silk Road site.
>> Silk Road web server administered over VPN from a server
>> VPN server IP stored in the Silk Road PHP source code
>> VPN server accessed from a location 15240 cm (500 ft) from a location that accessed the Ross Ulbricht GMail account.
The location of the Dread Pirate Roberts was something of an open secret. It is clear that he was based in the west coast of the US. Ulbricht was located in San Francisco at the same time as DPR, as proved by his large online footprint: Google+, YouTube, GMail.
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