Access to higher education varies across states for undocumented students (with or without Deferred Action for Childhood Arrivals [DACA]). In-state resident tuition policies (ISRTs) provide eligible undocumented students to pay in-state tuition rates at public universities and colleges. This qualitative study examines interviews from institutional agents and undocumented students at one institution to highlight how an ISRT policy is enacted by institutional agents and how undocumented students use their experiential knowledge to create unique approaches to navigate access to the policy. This research untangles the complexities of making policy decisions that dictate the educational experiences of historically marginalized populations. Situating the voices of institutional agents and undocumented students is significant to understand how institutional agents' actions can determine, disrupt, or empower the educational trajectories of undocumented students. ISRT and financial aid policies are situated within the epicenter of contradicting ideological and political landscapes of federal, state, and institutional policies and procedures. To enact these policies, institutional agents must navigate multifaceted contexts, including multiple layers of policy, their commitment to facilitate access to students, as well as their individual beliefs on immigration. Findings in this study uncover multiple approaches to policy compliance and how power and privilege can undergird enactment. Undocumented students highlight how institutional agents can use their privilege to support undocumented students by "finding loopholes," negotiating restrictive language in policy text, and cross-departmental collaborations to maximize access.