The present study investigated the progression from social skills knowledge and performance to becoming a high school dropout among first-year high school students. We also examine the mediating role of school satisfaction in the process regarding dropping out of high school. A total of 332 first-year high school students participated in a questionnaire survey in September, assessing school satisfaction, which consisted of a sense of approval and victimization in the class and social skills; 49 of the participants dropped out of high school at the end of the first school year. The results of categorical path analysis showed that social skills knowledge was positively correlated with social skills performance. Additionally, social skills performance was negatively correlated with dropping out of school. Moreover, the relationship between social skills performance and being a high school dropout was mediated by a sense of approval in the class. Finally, the discussion describes the need for support of social skills education to prevent first-year high school students from dropping out.