Purpose This study investigates the features of pragmatic and conversational skills in the language of Arabic-speaking adolescents with autism spectrum disorder (ASD) by comparing them with typically developing (TD) Arabic-speaking adolescents in Saudi Arabia. It aims to identify the differences in the pragmatic skills of the two groups and the perception of those skills by caregivers, with respect to four main pragmatic areas: discourse management, communicative function, conversational repair, and presupposition abilities. Method Data for this study were collected from 15 Saudi adolescents with ASD and a control group of 15 TD adolescents, matched for gender and language abilities. All the participants were in the normal IQ range. The caregivers of the adolescents with ASD and TD adolescents also participated in this study. Data were collected on the adolescents' performances using the Yale in vivo Pragmatic Protocol. In addition, the Pragmatics Profile of Everyday Communication Skills (PPECS) was used to collect data on the caregivers' perceptions of the adolescents' abilities. The combination of tools in this study allows for a unique comparison between actual performance and caregivers' perceptions. Results As expected, both the adolescents' performances and the caregivers' perceptions reflected an overall deficit in the pragmatic and conversational skills of adolescents with ASD. However, we also identified an inconsistency between the caregivers' estimation of the participant's pragmatic abilities and the actual abilities demonstrated by the adolescents. In particular, TD adolescents performed significantly better than adolescents with ASD in the pragmatic areas of turn-taking, topic maintenance, and topic initiation, but the caregivers did not detect differences between the two groups in these discourse management abilities. Conclusions This study has important implications for both ASD interventions and assessment. It provides a comprehensive assessment approach for measuring pragmatic skills, including both direct (participants' performances) and indirect (caregivers' perceptions) measures. Future research may benefit from adopting the combined approach used in this study to explore pragmatics in ASD. Differences between caregivers' perceptions and the performances of individuals with ASD should be considered, as well as the influence of various factors on their communication.