This paper reports research that investigated how digital technologies were used to develop and maintain home–school connections and develop positive relationships when children transition to nursery schools and schools. School case studies, comprising four purposively selected schools with nursery provision in Northern Ireland and four primary schools in New Zealand, provided the context and evidence to enable a small-scale comparative study of how digital technologies enabled the development of relationships between homes and schools over time. In this paper, the findings were analysed using a conceptual model and framework derived from earlier studies in this field. However, given the contemporary social and technological con-text, it was found that the framework could be reviewed and elaborated, enabling the creation of a new conceptual framework that is offered here. Our findings reveal methods of employing digital technologies to positively support parental engagement when children transition to nurseries and schools. From the analysis of our findings using the framework developed, points to consider for future practice, policy, and research are highlighted, with an emphasis on understanding and integrating parents’ aspirations into the transition process. Opportunities that use existing and emerging methods for home–school–community connections need to be made known to teachers and schools. While the digital technologies used must be capable of maintaining appropriate regular communication, additionally, the supporting ways for involving parental voice in reviews of existing practices and exploring new opportunities should be shared with teachers and schools. Future research should explore how the use of digital technologies in developing wider and deeper engagement and participation of parents and carers with nurseries and schools might lead to a longer-term and positive engagement in later years beyond nursery schools and the initial transition to school.