What Silk Road's Email Service Would Have Looked Like

It was supposed to pull people into the Silk Road ecosystem.

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Sep 11 2015, 3:37pm

Photo: Steven Tom/Flickr

Silk Road was only the beginning. As detailed in a Motherboard investigation, the owner of the now defunct drug marketplace, who went by the moniker Dread Pirate Roberts (DPR), and two of his secret employees, Variety Jones and Smed, were working to expand the business into an ecosystem of different services and products.

One of those was an anonymous Bitcoin exchange, another was apparently a secure phone service. But the project that seems to have gotten further than any other is an encrypted email service, referred to as "CryptoMail" or "Silk Mail."

In an email account belonging to Variety Jones, DPR's so-called "mentor," is a document laying out the plans for such a service, dated June 29, 2012. Other messages discuss the project's development and goals.

"I want to offer this to the public as a loss leader and a way to get them into the eco system," Variety Jones wrote to DPR, according to a message found in his email account.

Although the text makes no explicit mention of Silk Road, conversations between Variety Jones and DPR contained in the email account refer to "Silk Mail." The executive summary of the document says that "The public name will be more carefully chosen and this document will be updated as more technologies are added to the system."

The summary adds that "CryptoMail is a communication platform that emphasizes security and privacy."

This is evident from the design of the product. The main server would run as a Tor hidden service, "located in an undisclosed bulletproof hosting facility." Customers could either connect through a proxy site, or via Tor.

Logging of customer data would also be kept to a minimum, and "Web traffic logging will either be turned off completely or will never include any user-specific data, including IP addresses and usernames," the document reads.

The idea was to allow people with any level of security awareness to join

CryptoMail accounts would come in different "levels," with each providing additional services. At bottom, all accounts allow the automatic encryption of incoming mail, password resets are sent in an encrypted message, shared calendaring is available, and customers can also make use of Yubikeys, which are two-factor authentication tools.

There are some limitations, however, such as a 100MB storage limit, and no more than 10 messages can be sent per day, for the free accounts. A note next to this feature reads "Too strict?"

Higher tiers allow users to utilize an email client to access their account, and come with larger storage limits.

The idea, judging by the document, was to allow people with any level of security awareness to join, "although strong encouragement and admonishment will be made regarding security and privacy best practices." One diagram includes a "scoring system," with higher points being awarded for better security decisions.

The operators also wanted to monetize some of this assistance, by having customers pay for help on generating PGP encryption keys.

It's important to note that the document is riddled with "TO DO" notes, meaning that the project was most definitely a work in progress at the time. The section titled "Mobile Phones" is blank.

The creators were also keen to point out advantages they had over their competitors, such as Tor Mail, which was later seized in 2013.

(Other services called CryptoMail have been developed in the past, but appear to be unrelated to this project.)

Evidently, Silk Mail never came to fruition. Ross Ulbricht, the convicted creator of the Silk Road was arrested in October 2013, and no encrypted email service was launched. The current whereabouts of Variety Jones, who really pushed for this brand expansion, are unclear.