Vocational program-student mismatch is an important issue in secondary vocational education because students may enter programs that do not correspond with their initial preferences, shaping their subsequent learning experiences and career considerations. This study explored students’ experiences of vocational choice, learning, and career development in the context of program–student mismatch. A qualitative case study design was employed. An initial questionnaire was administered to approximately 300 Grade 10 students, followed by interviews with students identified as experiencing mismatch, supplemented by observation and school documentation. Data were analyzed through qualitative data reduction, organization, and interpretation. The screening identified 65 students (21.67%) whose current vocational program was not their first choice. Students’ accounts indicated that mismatch was shaped by parental and peer influence, limited information about vocational programs and career pathways, and limited understanding of their vocational interests and abilities. Students also described reduced motivation, difficulties engaging with vocational learning, and challenges in understanding vocational subject matter. The findings suggest that program–student mismatch is shaped by social, informational, and developmental conditions and may extend into students’ learning and emerging career considerations. The study highlights the importance of proactive career guidance, comprehensive vocational information, and continued counseling support.