The purpose of this study is to identify the factors of character education that affect students' self-regulation skills. Research uses a quantitative approach. The instrument used was adapted from SRLOQ, which was developed by (Vrieling et al., 2013), but modified with words to fit the context of this study. The research instrument consisted of two parts: measurement of self-regulation skills and student demographic information with a total of 108 students who took part in a character education training program at a high school in Islamic boarding schools. Data analysis involves t test, analysis of variance and multiple regression analysis. The results of this study indicate that gender and age have a strong and significant influence on self-regulation skills. Previous education was also found to have an indirect impact on self-regulation skills. This shows that age maturity is an important component of self-regulation skills, because the higher the age level, the higher the student's thinking ability. In addition, gender is also a component that affects self-regulation skills because there are differences in the way of thinking between men and women. The findings of this study indicate that self-regulation skills become dynamic entities especially with increasing age and gender differences.