Academic advising is one of the few ways that institutions of higher education exert influence on student success and retention, though the organizational conditions that promote these outcomes are not well understood in the literature or in practice. Nor is it clear how advisors come to understand their role and associated expectations. This qualitative case study examined the role of the professional academic advisor at a single institution through the lens of Role Theory (Rizzo & Lirtzman, 1976). Role Theory postulated that when employees experience ambiguous or conflicting expectations, this negatively impacts both work productivity and job satisfaction. Nine academic advisors chosen through purposeful sampling participated in an interview and a document analysis. Participants were asked about their roles and responsibilities and about the organizational context in which they worked. The study found that there were aspects of the role of the advisor that were clear. However, four organizational conditions were identified that created obstacles for academic advisors in carrying out their student success mission: academic advisors were isolated, lacked resources, had poorly defined roles and responsibilities, and had multiple and sometimes conflicting performance expectations. Future studies should evaluate the role of the academic advisor from a variety of novel lenses. Recommendations for administrators include connecting with the advising community, clarifying advisor role, and investing resources in advising. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]