This article describes the findings of a series of qualitative research studies which explored the technologies with which children aged 3–5 years old play, the forms of learning related to these activities, and the conditions which shaped their experiences with digital resources. Three forms of learning were observed in educational settings and an additional form identified when children engaged with technologies at home. However, the proactive support of adults was identified as crucial if children were to have the kind of positive encounters with technology that support learning. We found no evidence that playing with technologies dominated the everyday experience of young children, but their individual preferences, the attitudes of their parents towards technologies and ways of learning, and their family practices all made a difference to what was played and the opportunities for learning.