Purpose: An intervention package, including teaching break requests and tolerance for delay in reinforcement delivery to increase task engagement, was implemented with a 4-year-old child with an autism spectrum disorder who did not engage for a duration commensurate with individual education program team expectations. Method: A multiple-probe design across tasks was implemented. Dependent measures taken included engagement duration and the production of spoken break requests after work completion. Intervention was implemented with tasks involving short periods of engagement prior to the learner’s disengagement. The possibility of the learner’s overgeneralized production of break requests with tasks originally associated with longer engagement was also examined. Results: The participant learned to request breaks in short engagement tasks. In addition, engagement increased dramatically without off-task behavior. Overgeneralized use of break requests with long engagement tasks did not occur. Generalization of break requests to untrained short engagement tasks that were not the focus of intervention (but were associated with escape and short engagement) did not occur until the intervention package was implemented. Conclusions: The combination of teaching break requests and tolerance for delay in reinforcement delivery was effective in addressing problem behavior. Implications for enhancing properly generalized and moderated use of break requests across different tasks or contexts are discussed.