While peer interaction differences are considered a central feature of autism, little is known regarding the nature of these interactions via directly-observed measurement of naturalistic (i.e., minimally-structured) groups of autistic and non-autistic adolescent peers. 148 autistic and non-autistic adolescents (111 male, M = 14.22, SD = 1.90; M = 103.22, SD = 15.80) participated in a 50-minute, minimally-structured, naturalistic peer interaction paradigm with activities of varying social demands: an incidental social demand (eating in a room with peers), a physical social demand (playing a physically-interactive game), and a verbal social demand (playing a verbal game). While autistic youth exhibited fewer overall interaction behaviors than non-autistic youth, the two groups did not differ in amount of positive, negative, and low-level interaction behaviors. Within activities, autistic and non-autistic youth only differed in positive interaction behaviors during the context of a verbal social demand. Youth who displayed more positive interaction behaviors during this same activity had less autism spectrum disorder symptomatology, controlling for nested group effects and relevant covariates. These results point toward subtle differences in social demands across naturalistic settings that can either support or impede prosocial interaction for autistic youth, providing a guidepost for identifying settings that best promote social success for neurodiverse populations.