December 31, 2019

Decrypt: Ross Ulbricht and Silk Road

Grab a feel for Ross Ulbricht. Explore the timeline of Silk Road.

Decrypt the mysteries of the dark web

For those who haven't used marketplaces imagine an eBay for illegal activities; drugs, guns, weapons, passports and fake notes. Throw in the odd "Assassin / Hitman", that's what the FBI did to defame Ulbricht's reputation.

Buying something illegal, easily becomes exciting. Correction, it becomes addictive, it's a huge adrenaline rush compared to meeting your local not-so-hippy dealer - Watch a BBC employee order from a marketplace

Here is Ross William Ulbricht

Video published by the Free Ross campaign, over a quarter of a million signatures.
Follow Ross on Twitter to read regular handwritten letters.

Leave your mark on the petition to free Ross

The inventor of the first modern marketplace

August 2010 - Ross starting coding Silk Road
Ross struggled with coding. A novice. He felt he could not trust anybody else to code his vision, therefore he decided to request assistance in online forums on the Clearnet. He used identifiable information.

January 2011 - Silk Road Launch Day
It's hard enough gaining traffic to a Clearnet site (appreciate you), exceptionally difficult attracting attention to a lengthy  .onion address

27th January 2011 - Ross uses an alias "Altoid" to advertise - "I came across this website called Silk Road. I'm thinking of buying off it... Let me know what you think." on a public forum targeting magic mushroom consumers

29th January 2011 - "Altoid" posts "Has anyone seen Silk Road yet? It's kind of like an anonymous I don't think they have heroin on there, but they are selling other stuff"  on Bitcointalk

These posts are still available on the Clearnet

11th October 2011 - "Altoid" posts "I'm looking for an IT pro in the Bitcoin community to hire in connection with a venture backed Bitcoin start-up company. Interested parties should contact" on Bitcointalk

These posts are still available on the Clearnet

It was the start of Silk Road, which led to Ulbricht's unfortunate discovery.  
Was it simply a lack of experience, or common disregard? I believe Ross was slightly naive.

Screenshots of all posts by "Altoid":
Desktop (Large resolution): Page 1 | Page 2 | Page 3
Mobile (Small resolution): Page 1 | Page 2 | Page 3

Aug 2010 - Oct 2013 - Ross leaked small pieces of information
Ross frequented the same cafés and libraries. He used VPNs to create a false IP if traced via Geolocation. Records and log files (Google's) showed Ulbricht regularly logged into - which was traced back to the same day and time Ross was using the VPN.

March 2013 - It's rumoured to be Ross requesting help on Stack Overflow.

Desktop (Large resolution): Page 1
Mobile (Small resolution): Page 1

In Hindsight
While Ross fundamentally practised decent elements of OPSEC, he lacked in:
- Deleting logs of VPNs / Rotating VPNs - providers, patterns, encryption
- Email addresses linking with identifiable information / other nicknames  
- Allowing himself to be identified through [email protected]
- Discussing his success on Linkedin
- Becoming predictable; routine, location and browsing habits
- Reusing the same alias / nicknames - portraying different personas
- Failed to create regular disposable / "throwaway" accounts
- Using a service which refuses to respect privacy - Google (decent alt.
- Accessing dark web on public networks - read on packet analysing and sniffing
- The @gmail leaks allowed FBI to gain traction on interests, YouTube history
- VPN company was subpoenaed by FBI to give details - logs, original IP
- Trusted the wrong services - self-host!

The government intercepted 9 counterfeit IDs, posted from Canada to an address in San Francisco. Ross was greeted by law enforcement when they followed the route.

Ultimately Silk Road grew too quickly for Ross to manage; the servers, users, sellers, transactions, reviews - abolishing the bad sellers. He had the infrastructure without a large enough team to expand.

Who could he trust?! - Ross learned to trust a few selected people, some have never been caught.

Huge addictive adrenaline. The rush. The greed, for more.

The crafty FBI predicted his movements and waited for Ross to have Silk Road /admin open in the public unencrypted.
Simple game plan to stage a public disturbance, a classic distraction tactic. This caused Ross to become distracted. Simply swooping in ...

October 2013 - The arrest
— Ross connects to Wi-Fi
— Cirrcus (Moderator of Silk Road) "Are you there?"
— Ross: "Hey"
— Cirrcus: "Can you check one of the flagged messages for me?"
—  Ross: "Sure. Which post?"
*Ross connects to /admin*
A man and woman starts arguing, within Ulbricht's personal space.
Ross turns around, to face the couple. The man proceeds to push Ulbricht's laptop across the table - the woman grabs the laptop and hands it to an FBI agent.

Ross was arrested, placed in handcuffs.

Stay safe!

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