At four years of age, young children in government-funded preschool programs are suspended or expelled from school more frequently than their school-aged counterparts. These students comprise a largely minority enrollment that does not reflect the demographic of the teachers and administrators implementing the preschool program. The purpose of this case study research was to investigate the trend of behavior-related expulsions in a government-funded preschool program and to examine the impact of culture on this phenomenon. The study examined the lack of cultural responsiveness as a potential barrier to student success. Research literature provides common strategies to address the dual concepts of self-regulation and cultural competence. The findings of this study suggest that preschool administrators perceive similar linkages to solve the dilemmas of cultural dissonance and underdeveloped self-regulation of preschoolers in the classroom. However, the observed classes revealed few culturally competent practices to foster the self-regulatory skills needed to reduce preschool failure. This research indicates that awareness-building is required for school administrators to advance leadership toward a more culturally competent schooling environment