While most community college students express a desire to transfer to a four-year college or university, only a quarter of them end up transferring (Horn & Skomsvold, 2011; Hossler et al., 2012; Jenkins & Fink, 2015; Shapiro et al., 2013). This could be in part because the transfer process has become more complex (Bragg, 2017), especially for states with institution-driven systems where articulation is primarily driven by four-year colleges and universities (Hodara et al., 2017). This qualitative study sought to understand the experiences of community college academic advisors who advise transfer students in their pursuit of earning a baccalaureate degree. Using a pragmatic approach and Hodara’s et al. (2017) framework for statewide articulation systems, 12 community college academic advisors were interviewed across the state of North Carolina to further understand how they experience their statewide articulation system when advising transfer students. Three themes were identified from the 12 interviews: student challenges and complexities, campus challenges and complexities, and system challenges and complexities. Implications of the study require that community colleges consider how to improve advising on their respective campuses, determine ways to better utilize and improve ACA 122: College Transfer Success, and address gaps in North Carolina’s Comprehensive Articulation Agreement.