This paper is based on a presentation given at the ‘Rethinking Literacy, Digital Competency and Media Education in the Age of Digital Platforms’ webinar hosted by Gyeongin National University in September 2020. In the paper, I explore the difficulties of implementing ‘critical data education’ programs in schools with children and young people. Reporting on three research projects with over 150 Australian students (aged 8-16 years), I explore the challenges and opportunities that arose. Each project was based around an educational chat app designed to develop young people’s understandings about the role that digital data now plays in their everyday lives – especially in terms of the data economy and dataveillance. The findings highlight the technological, ethical and social issues encountered and the need for data education programmes to articulate with young people’s expectations for media use. The paper concludes by considering how this might be achieved in schools through re-imaging the dominant forms of digital ‘cybersafety’ education in schools.