Children and youth socialize, interact and engage both in offline as well as online environments. These interactions are mediated by technology, are marked by the production of large amounts of (meta)data and have intensified children’s and youth’s experiences of/with the digital giving ways to what researchers have described as datafied childhoods (Mascheroni, 2020). A big part of datafied childhood is dataveillance (Van Dijck, 2014), that is the surveillance of people based on their online data; however, notwithstanding calls for a more critical examination of children’s and youth’s lived experience with digital surveillance and its implications for children’s rights as data subjects (Lupton & Williamson, 2017), little is known on how children and youth make meaning of and engage as watchers and watched in acts of dataveillance and self-surveillance. This paper presents preliminary findings of a small-scale qualitative study on youth’s practices and experiences of digital surveillance. Using personal interviews, focus group interviews and a speculative design component with 15-19 year-old participants, we sought to explore how children and youth in Cyprus understand and practice acts of digital surveillance as part of a broader question on the reconstitution of childhood as a result of digital surveillance technologies (Marx & Steeves, 2010; Steeves & Jones, 2010).