New research shows that adult participation in children’s play is beneficial for learning and development in early childhood. It is particularly socio-dramatic narrative play, in which children and adults co-construct the play events that is beneficial. Research also shows that teachers in the Swedish preschool tend not play with children. The Swedish Education Act and the Swedish Preschool Curriculum contain goals to strive for, specifically regarding play. Greater efforts and insight is needed to pave the way to increase the benefits for children through the use of play (Broström, 2017). The purpose of this study is to develop knowledge that contributes to understanding of the relationship between pretend play and children’s’ learning and development, as well as the development of preschool didactic and pedagogical activities based on this knowledge. To achieve this aim we drew on Cultural Historical Activity Theory to develop and conduct a case study at a municipal preschool. Data was gathered through observations of preschool children and staff in two units and through individual, semi-structured interviews with eight preschool teachers. We found that the preschool teachers rarely engaged fully in children’s play; however, when they did engage with the children in play, their involvement ranged from a slight involvement, to being a stage hand in the play, or being passively engaged in joint play with children. Our cultural-historical analyses revealed mediating activities that have an effect on if and how teachers engage in play with children. We conclude by arguing that teachers need more education about what type of adult child joint play that is beneficial and that the preschool directors have an important job to help manage the preschool teachers time and provide opportunities for them to reflect and document their work in such way that more time could be set apart for them to commit to being fully engaged with children in narrative pretend play.