There is increasing recognition of digital childhoods [Danby, S., Fleer, M., Davidson, C., & Hatzigianni, M. (Eds.). (2018). Digital childhood. Amsterdam: Springer] and a corresponding body of research into young child's engagement with digital devices across a broad range of contexts [Marsh, J. A., Plowman, L., Yamada-Rice, D., Bishop, J., & Scott, F. (2016). Digital play: a new classification. Early Years, 36, 242–253. doi:10.1080/09575146.20161167675]. What is missing from the literature is an understanding of if and how these devices, when used with animation apps in play-based programs, change pre-school practices and the developmental conditions of children's play. In drawing upon Vygotsky's [(). Play and its role in the mental development of the child. Voprosy Psikhologii, 12, 62–76] conception of play as the leading motive of pre-school-aged children, the naturalistic study reported in this paper seeks to address this gap. Video observations of children (3.3–5.8 years) and teachers digitally engaged across five sites during free-play time (413.8 h of video observations) were studied using a cultural–historical conception of play [Vygotsky, L. S. (2005). Appendix: from the notes of L.S Vygotsky for lectures on the psychology of preschool children. Journal of Russian and East European Psychology, 43, 90–97]. The findings show that digital animation in a free-play program where role-play is featured can enrich the play opportunities of children which in turn promote play complexity and increase social and cognitive demands on children, which together can be theorized as a positive force for children's development. These developmental conditions emerged as a profile of five interrelated key digital practices and psychological characteristics, adding to our understandings of digital play.