The high dropout rate of the United States Virgin Islands school district's ninth-grade students is a major educational problem and the catalyst for a myriad of social problems. Ninth grade academies and extended school day intervention programs have benefited only the academically prepared students. This qualitative case study examined educators' perceptions of the challenges that led to the increased dropout rate of the district's ninth-grade students. Bandura's self-efficacy theory and Atkinson's motivational achievement theory formed the foundational pillars for this study. The research questions were focused on challenges that led to the increased dropout rate of ninth-grade students and the programs implemented to support dropout prevention. The data collection methods consisted of questionnaires from 4 administrators, 4 counselors, and 16 core-subject teachers, and semi-structured group interviews with 2 administrators, 2 counselors, and 8 core subject teachers. Analysis of the data included coding and the identification of common themes. The findings showed that poor school attendance, academic unpreparedness, and disciplinary infractions were some of the challenges that resulted in premature school dropout. Interpretation of the data confirmed that the implementation of proactive and reactive approaches, modified instructional methods, and intervention strategies have proven ineffective. After 10 years, the ninth grade academies of the school district have had no significant effect on promotion or retention rates. The introduction of Ninth Grade Completion via Career Curriculum Academies, a combination of college preparatory and vocational skills classes, may transform education for ninth-graders, increase promotional rates, and benefit the larger community.