Dutch non-government organisation Terre des Hommes in 2013 identified over a thousand predators seeking to engage in Webcam Child Sex Tourism from some 65 countries over a period of about 10 weeks. These were among 20,000 requests directed to a fictitious 10-year-old Filipina girl, really a 3-D avatar called “Sweetie”, operated by a team of Terre des Hommes researchers. Numerous referrals to police and prosecutions followed, the first resulting conviction being that of an Australian citizen in 2014. A more sophisticated and automated version of the virtual girl, “Sweetie 2.0”, now operates independently as a chatbot with enhanced detection functionality to recognise indecent online behaviour and chat characteristics associated with individuals, which can be stored and analysed for matching with chat records held or obtained by law enforcement or third parties. These developments illustrate the expanding scope for automated detection of cybercrime, including online child exploitation that might be an important element of future policing. However, most legal systems are not yet ready for automated surveillance devices such as “Sweetie” to be used by law enforcement, with open questions about the legality of their use and the admissibility of evidence thereby obtained. The presentation discusses the findings of the 2016 report entitled ‘Legal Aspects of Sweetie 2.0’ commissioned by Terre des Hommes comparing the laws of nearly twenty countries, against the substantive and procedural frameworks of their domestic legal systems as well as key international agreements such as the Council of Europe’s Convention on Cybercrime and the Lanzarote Convention