This article explores the nature of teachers' involvement in child-managed play. We approached this didactic issue through analysis of interactional situations in a kindergarten and an after-school programme and by drawing on relational theory and the concept of "pedagogical tact". Qualitative material was gathered from observations and video recordings of children and their teachers in the kindergarten and the after-school programme, and interactional situations were analysed. The findings show that in both institutions, teachers' involvement follows three main approaches: surveillance, an initiating and inspiring approach, and a participating and interactional approach. Whether surveillance is based on judgments about safety or about rules, it seems to hamper the children's play. Children in both institution types seem to like when teachers' involvement included the initiation of new activities. Such activities often transform into child-managed play. Teachers' inspiring communications and interactions were also characterised by recognition and acknowledgement, and this approach appeared to promote child-managed play. It seems important that a surveillance approach does not overshadow an initiating and inspiring approach or a participating and interactional approach in interactional situations through which teachers act with pedagogical thoughtfulness and tact.