Complex care management (CCM) interventions have been developed across the United States to address the challenges of high-need, high-cost patients. Though their heterogeneity makes it challenging to determine their general effectiveness, there are calls in the literature to continue to implement and evaluate them. This article presents CCM patient and care manager perspectives on facilitators and barriers to success in such a program in a safety-net hospital. Our findings suggest that motivated patients, team-based care, and the ability to form trusting, supportive relationships are important contributors to success in a CCM program while patients' own mental health and socioeconomic challenges impede success. Given the relatively short-term nature of most CCM programs and the complicated challenges faced by many CCM patients, this work poses larger questions to consider around the general alignment of the program model to the patient population and the definition of success for CCM programs.