This study examined stereotypy in naturalistic classroom contexts (i.e., academic programming, leisure skill acquisition) with differential reinforcement of contextually appropriate behavior (DRA). When stereotypy was problematic, redirection to the ongoing activity was provided. Contextually appropriate behavior and stereotypy were measured across all contexts prior to redirecting stereotypy to contextually appropriate behavior. Low levels of stereotypy were observed during the DRA in at least 2 contexts for all 5 participants. Context-specific redirection was added to the DRA if stereotypy persisted, and decreased stereotypy in 9 of the 10 evaluations. The results suggest that stereotypy might not be problematic in all contexts when DRA is present and redirection to contextually relevant appropriate behavior is an effective strategy.