Amid persistent rises in college tuition over the past several years, financial aid policy has marched steadily toward goals of making college more affordable and removing economic barriers to attendance. Promises of "free college" often target low- and middle-income students, and likely have a particular influence on: (a) students who will be the first in their families to enroll in and graduate from college, (b) recent immigrants, (c) English language learners, and (d) students of color. Despite the central role that counselors and college advising professionals play in the college access pipeline, very little is known about how college advising practitioners make sense of financial aid policies and the ways financial aid policies shape interactions with students and families in the educational pipeline. This study sought to address that gap in the literature drawing upon sensemaking theory (Spillane et al., 2002) and qualitative case study methodologies (Merriam, 1998; Merriam & Tisdell, 2015; Yazan, 2015). Data included interviews with practitioners and field observations at public financial aid events in an urban area in southern California during the 2022-2023 academic year. Findings revealed: (a) the key role students' and families' prior knowledge and beliefs about financial aid policies play in their pursuit of college, (b) multiple ways in which financial aid policies orient and constrain interactions between students and practitioners, and (c) practitioners' self-perceptions of possessing inadequate training and expertise to advise on financial aid policy competently. This study identified strategies and considerations for practitioners and policymakers to maximize students' and families' successful navigation of their financial aid and college choice journeys--no matter where they ultimately decide to go. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]