Social skills deficits are commonly reported among children with social phobia (SP) and children with Asperger's Disorder (AD); however, a lack of direct comparison makes it unclear whether these groups, both of which endorse the presence of social anxiety, have similar or unique skills deficits. In this investigation, the social behaviors of children with SP (n = 30) or AD (n = 30) were compared to a typically developing (TD) peer group (n = 30) during structured role play interactions. Data were analyzed using blinded observers' ratings of overt behaviors and digital vocal analysis of verbal communication. Compared to children with AD and TD children, children with SP exhibited less overall social skill, an ineffective ability to manage the conversational topic (pragmatic social behavior), and deficient speech production (speech and prosodic social behavior). There were no differences in observer ratings between children with AD and TD children. However, using digital analysis of vocal characteristics (i.e., intensity, pitch), distinct vocal patterns emerged. Specifically, children with AD spoke more softly than TD children, and had lower vocal pitch and less vocal pitch variability than children with SP. This pattern may be subjectively heard as monotonic speech. Consistent with a vocal pattern associated with heightened anxiety, children with SP spoke more softly and had less voice volume variation than TD children, and had higher vocal pitch and more vocal pitch variability (jitteriness) than children with AD. Clinical implications of these findings are discussed.