We extended research on social skills training to determine if the activities first-grade students were engaged in while Tootling would influence their performance of two recently trained social skills: complimenting and encouraging peers. After receiving social skills training, students engaged in two experimental small-group activities, a cooperative activity and a parallel-play activity. During both activities, a Tootling intervention was applied and interdependent group rewards (e.g., every student in the class receives the reward) were delivered contingent upon the number of peer reports of classmates providing compliments and encouragements meeting an unknown, randomly selected criterion. Students also engaged in their typical classroom activity, an individual competition, without Tootling. Statistical analysis indicated that during the cooperative-play activity there were significantly higher levels of complimenting and encouraging than during the parallel-play and individual competition activities. More compliments were delivered during the parallel-play activity than during the individual competition, but there was no significant difference in encouragements across the two conditions. Also, during the parallel-play activity, compliments where higher than encouragements. These findings suggest that after social skills training, Tootling can enhance social skill performance when educators schedule activities that provide opportunities to engage in these recently trained skills. Discussion focuses on task and goal structures associated with activities and applied implications for enhancing social skill development.