Autonomous cyber capabilities (ACC)—software agents programmed to operate through cyberspace without real-time human oversight or intervention—are slowly becoming a tangible reality. States and regional organisations are increasing investment in the research and development of these technologies for both offensive and defensive applications. So far, discussions surrounding cyberspace and autonomous systems have neglected this emerging area. This chapter aims to fill this gap by exploring whether, and to what extent, ACC can be deployed to execute autonomous cyber attacks in compliance with targeting rules under International Humanitarian Law (IHL), focusing on the fundamental principles of distinction, proportionality, and precaution. Specifically, it considers ACC’s application in deliberate and dynamic cyber attacks. It argues that, depending on the operational circumstances, a wide range of precautionary measures can be implemented to ensure that ACC accurately identify targets while avoiding or minimising incidental collateral damage. These measures range from embedding technical safeguards to retaining human control over ACC during deployment. As military reliance on autonomous technologies increases, this chapter highlights the urgent need for further research to address the operational and legal challenges posed by ACC in future warfare.