Objective: Accelerated Second-Degree (ASD) programs play a crucial role in addressing the nursing shortage. However, when ASD students drop out, it negatively impacts all involved parties. Despite facing similar challenges as adult learners, some ASD students successfully graduate while others do not. By comparing and contrasting these two groups, we can explore their similarities and differences, support future students' success, and ultimately alleviate the nursing shortage. Participants: For this study, we purposefully selected 17 cases of ASD students with information-rich backgrounds. These participants attended seven different universities across three states and either completed or dropped out of the ASD program within two years of the study. Study Method: We conducted a qualitative comparative cross-case study using semi-structured interviews to retrospectively explore students' experiences and outcomes. Findings: Our analysis revealed five overarching themes: the complex interrelationship of factors, the non-binary definition of success, and 17 factors grouped into external, institutional, and personal categories. Conclusions: Each of the 17 external, institutional, and personal factors is critical to students' experience and outcome. However, assigning supportive and impeding values requires examining them within the context of their interrelationship with other factors on a case-by-case basis. By leveraging supporting factors against impeding factors, stakeholders can increase students' chances of success. Simply counting impeding factors cannot predict failure, while multiple supporting factors do not guarantee success. Ultimately, students personally define success according to the context of their lives without limiting it to the duration or completion of the program. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]