Examining responses to violations of communication may provide insight into children’s communicative competencies not apparent during reciprocal interactions. In this study, the caregivers of 18-month-old typically developing children, 30-month-old children with autism spectrum disorder (ASD), and 30-month-old children with Down syndrome followed our suggestion to playfully violate communication with their children in two contexts: requesting and social interacting. Caregivers of children with ASD made fewer bids and violations, which their children accepted less often than typically developing children; they also used instrumental behaviors more often when responding. Children with Down syndrome responded to their caregivers similarly to typically developing children, and used more high-level communicative behaviors in the requesting, versus social interacting, context. This study highlights the bidirectional nature of parent-child interactions, and suggests that violations of communication may serve as a “press” to elicit child behaviors not present during reciprocal communication.