This paper is a contemplation of a digital ethnography with the community surrounding Silk Road, the first widely used cryptomarket for drugs on the Dark Web. To position the study within the broader field of illegal anthropology, it provides links between the existing literature on the study of cryptomarkets with relevant anthropological scholarship. A theory of piracy is interrogated for its explanatory capacity of the digital pirates of the Dark Web. The start of the study unexpectedly coincided with the FBI seizure of Silk Road in October 2013. The field site disappearance provoked a practice-based and conceptual rewiring. The paper unpacks how the ‘hydra effect’ introduced to conceptualise resilient innovation within cryptomarkets can also apply to the multiplicity of identities linked to research practice. This effect also raises how the knowledge production within digital ethnographic practice may be reconfigured through notions of opportunism, replication, obsolescence, regeneration, iteration, adaptation and proliferation.