This study aims to validate an automated social skills training (SST) system designed to assist individuals with distinct social communication challenges. Specifically, it targets those diagnosed with schizophrenia, who often struggle with social withdrawal, flat affect, and difficulty in interpreting social cues, as well as individuals with autism spectrum disorder, who typically face challenges in understanding nonverbal communication, maintaining reciprocal conversations, and adapting to social norms. The system is intended to help these individuals objectively assess their social interactions, learn appropriate social cues, and develop strategies to improve their communication skills in various social contexts. We conducted two key verifications: (1) comparing the improvement in social skills between a group of healthy adults trained with our SST system and a wait-list control group of healthy adults who received no intervention during the study period and (2) assessing the effectiveness of our SST system compared to traditional human–human SST. This chapter presents an analysis of the first verification, which has been completed, and outlines the experimental design for the second, which is currently in progress. Our findings demonstrate the effectiveness of the automated SST system over a four-week training period, with significant improvements in general self-efficacy, reduction in state anxiety, and enhanced speech clarity in the trained group.