Social pretend play may have a positive impact on children’s social development because it involves positive peer interactions and challenges their social-cognitive abilities. The current study aimed to investigate whether variations in play tutors’ active support and play management are associated with variations in children’s social pretend play level in the context of a pretend play tutoring intervention. Moreover, the moderating role of children’s social skills (cooperative behaviour and sociability) was examined. In total, 50 children from eight playgroups participated in the study (50% females, mean age at T1 = 46.6 months, SD = 4.3). Six play tutoring sessions took place during normal playgroup sessions (30–40 minutes each). Both the play tutors’ active support and play management and the children’s social pretend play were videotaped and rated for each 10-minute interval. Furthermore, teachers rated children’s social skills before the intervention. The study showed that active support – but not play management – was positively associated with children’s social pretend play level. Furthermore, children’s sociability positively predicted children’s social pretend play level during the intervention and also intensified the positive effect of active support on children’s social pretend play level. In contrast, children’s cooperative behaviour was not significantly associated with their social pretend play level. These results suggest that play tutoring in a group setting needs to be tailored to children’s needs and should actively aim to include withdrawn children, so that they can also profit more strongly from the intervention.