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Student or program deficiencies are the classic explanation for student departure from community college partners of career technical education programs. However, a complex set of factors impact college attendance, persistence, and departure decision-making. Participants' experiences both within and outside program structures can reshape long-term goals. Based on a seven year study of a population of 256 students, this article examines detailed case studies of two students' experiences leaving and reentering community college. It reveals how one program supported multiple exit and entry points. Interconnected educational and career pathways were made visible with the creation of a visual model that situated program experiences in a broader educational and career pathway. Additionally, both the use of creative solutions and adherence to rigid program parameters impacted students' career and educational trajectories. For more effective results, programs should support parallel career planning and encourage participants to question program structures in relation to their needs.