The use of tablets in a Greek kindergarten class (16 children aged 4–5) under the digital play framework (Bird & Edwards, 2015) is explored in this study. The Vygotskian framework was adapted with permission in the Greek language and socio-cultural context. The aim was to understand children's use of new, touchscreen technologies, but also to identify a useful way to observe the progression of that engagement. The project lasted for 4 months and children were observed ten times (written and video recorded observations). Children were observed in pairs or small groups during their free play with the tablets. Findings suggest that the adapted framework was particularly helpful, when observing children, but could benefit from more flexibility and a less linear structure. Children went through the different stages of the framework using social scaffolding as their most dynamic strategy. This study is significant as it reports on an underexplored context going through a range of social and political transformations (Greece), but also because it provides further insights on how to more efficiently document and assess children's play with technology.