This article follows the journey of creating a digital preventative education programme for combating online child sexual exploitation and abuse (OCSEA) and child sex trafficking in Thailand and Cambodia. Created and rolled out over 2 years as part of the End Violence Against Children (EVAC) grant during the COVID-19 global pandemic, this article sets out how the programme was designed, with direct input from children and professionals, and underpinned by human rights and contextual safeguarding principles. It outlines how collaborative approaches between children, academia, expert NGO’s, and professionals have resulted in a thought-provoking digital programme (May and Bay) that sensitively tackles sexual grooming and promotes child safeguarding. The article highlights how the game focuses on the interplay between children’s choices online and the environmental constraints they face, with the lead characters May (aged 11) and Bay (aged 13) making ‘risky’ and ‘safe’ choices against interacting aspects of their social and digital environments. The game supports the development of digital competence among children and professionals by promoting awareness of online harms emanating from the interplay of technology with children’s micro, meso, and macro environments against a range of people whose interaction with them may be ‘safe’ or ‘unsafe’. It recognises children, peers, parents, carers, professionals responsible for safeguarding, media, legislators, and local non-governmental and international aid organisations as potential ‘attractors’ or ‘agents within the system’ whose combined efforts can change how child safeguarding systems respond.