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This chapter focusses on the ethical issues raised by different types of surveillance and the varied ways in which surveillance can be covert. Three case studies are presented which highlight different types of surveillance and different ethical concerns. The first case concerns the use of undercover police to infiltrate political activist groups over a 40-year period in the UK. The second case study examines a joint operation by US and Australian law enforcement agencies: the FBI’s operation Trojan Shield and the AFP’s Operation Ironside. This involved distributing encrypted phone handsets to serious criminal organisations which included a ‘backdoor’ secretly sending encrypted copies of all messages to law enforcement. The third case study analyses the use of emotional artificial intelligence systems in educational digital learning platforms for children where technology companies collect, store and use intrusive personal data in an opaque manner. The authors discuss similarities and differences in the ethical questions raised by these cases, for example, the involvement of the state versus private corporations, the kinds of information gathered and how it is used.