The purpose of this exploratory case study was to understand the academic disengagement and reengagement process from the perspective of students enrolled in a dropout recovery charter school. Specifically, this study focused on students' perceptions of the factors that influenced their lack of success in the traditional school setting, the motivational factors that led them to enroll in a dropout recovery charter school, and the factors currently promoting their success in this new school setting. Thirteen students participated in semi-structured focus groups. Behavioral and discipline challenges and lack of teacher support were mentioned most frequently as barriers to success in the traditional school setting. Referrals by family, friends, or school staff and self-determined motivation were the most commonly reported motivators to enroll in the dropout recovery charter school. Students reported individualization of learning, school structure, and school climate as factors promoting their current success. The findings of this study have important implications for social work practice, particularly around social worker's engagement in multilevel systemic change, collaborative work with teachers, and the design of dropout prevention programs.