Nationally, while the majority of community college students indicate a desire to transfer to a four-year college or university, many of them fail to do so (Horn & Skomsvold, 2011; Hossler et al., 2012; Jenkins & Fink, 2015; Shapiro et al., 2013). Since the transfer process has become more complicated (Bragg, 2017), many states have developed statewide articulation systems to help mitigate issues related to credit efficiency and to streamline the transfer process (Anderson, 2018). However, transfer students are still taking longer to graduate and have to manage issues related to credit mobility, including excess at graduation and loss of hours and applicability during transfer (Hodara et al., 2017). To help us understand how transfer students are academically advised for the transfer process, this qualitative study explored the experiences of community college academic advisors who advise transfer students in their pursuit of earning a baccalaureate degree. It also offers a rare study of the academic advising process from the perspective of community college academic advisors and how they interact with transfer policy on a day-to-day basis. This study draws upon interviews with 12 community college academic advisors across the state of North Carolina to further comprehend how they experience their statewide articulation system when advising transfer students. The findings from the study detail how community college academic advisors cope with and navigate student, campus, and system challenges and complexities. Implications of the study require that community colleges consider how to organize academic advising on their respective campuses, determine how to improve interventions and programs to educate transfer students on transfer policy and process, and address gaps in North Carolina’s Comprehensive Articulation Agreement.