Objective/Research Question: This practitioner-scholar study investigated perceptions and experiences of community college students who transferred upon completion of their associate degree programs in Colorado, a state with multiple state-level transfer policies. Each student participated in a cohort-based transfer support program offered at their community college. The research questions were: (1.) Do community college students who participated in transfer programing while earning their associate degree perceive that it helped prepare them for successful transfer? (2.) Do community college students perceive that their courses prepared them to be successful at a university? (3.) What are the perceptions and experiences of community college students who transferred upon completion of their associate degree programs within a context of a state with multiple transfer policy initiatives? Methods: This study used a phenomenological approach and qualitative data collection methods. Results: While students believed their community colleges prepared them academically, and their transfer preparation programing was beneficial, their reflections highlight that regardless of support provided, academic preparation, or policy context, transfer from community college to university is challenging, problematic, and bureaucratic. Often community college students are viewed with a deficit lens by university staff. Conclusions/Contributions: Regardless of state policy context, transfer preparation, and support, obstacles encountered in the transfer process from community college to university must be negotiated through relationships and advocacy both on the part of college staff and the students themselves. However, students who transfer from a college with dedicated transfer support and preparation demonstrate resilience to complete the process successfully.