Silk Road is very interesting from a design perspective, particularly the way it leverages different open source cryptographic tools to satisfy its complex security/privacy/anonymity requirements.
I gave a talk about this at the Oakland Cryptoparty back in October. The slides are a little patchy and based entirely on perusing the site (read: speculation), but it inspired a lively discussion from amongst all the participants. It seems there's nothing like illegal drugs and the black market to get people interested in learning more about crypto!
I'm planning on giving an updated version of this talk at "SF Cryptoparty II" on March 23rd (attend or sign up to talk! https://cryptopartysf.org/). I will definitely incorporate ideas from (and link back to) this article. Feedback appreciated!
I think your Farmer's Market summary is outdated: it used Tor hidden service, for a short period only and after the investigation started (reading the indictment), and it's pretty clear now that Hushmail rolled over and then the garnered information was used to extract the Paypal & Western Union financial transactions. See my discussion of Farmer's Market in OP.
Slide 14 should mention the SQL injection attack on SR back in November or December 2012; I also disagree that DDoSes would be ineffective.
Slide 23: IIRC, someone has a verifiable anonymous mixer. I forget its name because it charges more than others.
Slide 27: Mtgox has been hacked and lost bitcoins, but haven't they always made up their users' losses? That's pretty important.
I gave a talk about this at the Oakland Cryptoparty back in October. The slides are a little patchy and based entirely on perusing the site (read: speculation), but it inspired a lively discussion from amongst all the participants. It seems there's nothing like illegal drugs and the black market to get people interested in learning more about crypto!
I'm planning on giving an updated version of this talk at "SF Cryptoparty II" on March 23rd (attend or sign up to talk! https://cryptopartysf.org/). I will definitely incorporate ideas from (and link back to) this article. Feedback appreciated!
Slides: http://garrett.im/static/pdf/silkroad_oakland_cryptoparty_sl...