The present study examined the behaviors of parents and children during a free play interaction in 20 children with high-functioning autism (HFA) and 20 matched, typically developing children. Observational coding was used to measure sensitive versus controlling parenting behaviors as well as children's responsivity and interest and investment in play. The study also documented whether the child or the parent primarily directed the play interaction. Finally, the study examined the influence of parenting stress on parents' behaviors during play. Group differences in behaviors were assessed along with associations between parent and child behaviors. Further, sequential analyses were conducted to identify whether parent behaviors temporally facilitated children's responses and interest during a play interaction. Results demonstrated group differences in parental sensitivity, parenting stress, child responsivity, and proportion of child-directed play. Parental sensitivity was also associated with child interest and investment as well as the proportion of child-directed play. Finally, sequential analyses demonstrated a temporal association between completely child-directed play and child interest and investment, and between parental sensitivity and child responsivity. These results extend the existing literature on the behaviors of children with autism and those of their parents within play settings, and have important implications for parent-focused play interventions.