Two preliminary pilot phases of a peer-mediated social skills program—Stay, Play, and Talk—within inclusive early years settings in Ontario, Canada, investigated changes in observed social interactions and perceived social skills. In Phase 1, a single-subject AB design demonstrated increases in total social interaction units for two of three kindergarten participants during structured activities, and pre- and post-intervention educator ratings demonstrated small social skill increases with peers for all three participants. In Phase 2, pre- and post-intervention educator ratings for nine participants in a group design demonstrated increases in play interaction and disruption and decreases in play disconnection, with a large effect size for increases in play interaction. Findings suggest that program participation within structured settings may support social skills gains for children with social communication difficulties.