Jon Lackman, art historian and writer, tells the story of RDS, Random Darknet Shopper, a bot created by the Swiss artists Carmen Weisskopf and Domagoj Smoljo, known as !Mediengruppe Bitnik. RDS is a piece of software that can operate nearly autonomously, blindly selecting an item costing less than $100 from an online black market, then paying for it from its own Bitcoin account, and having the item shipped to the address of the gallery or museum in which RDS resides at the moment. Its story began in September 2014, in an art gallery in St. Gallen, Switzerland, when it first bought a “Fire brigade master-keys set”. Since then it has bought many illegal items, such as counterfeit brand clothes, drugs, passport scans or credit card numbers. The shopping has been exhibited in the gallery and some paradoxical problems were raised when the police sequestered the Ecstasy pills. Is it illegal for a bot to randomly buy illegal items? And what happens when a vendor knows what (or who) RDS is?