Background: Promise programs have grown exponentially. Yet, we are still learning how systemic barriers affect promise program students’ abilities to meet promise program requirements and their postsecondary goals. Objective: The Degree Project (TDP) in Milwaukee, Wisconsin, was the nation’s first randomized control trial of a promise scholarship. Thirty-six high schools were assigned to control or treatment group and the TDP scholarship was available to any of the 2,587 ninth-grade students in the 18 treatment schools. As students experienced senior year, our aim was to understand more about the mechanisms in a promise context, such as the extent to which promise students in their senior year of high school would share any particular norms and resources received and used toward postsecondary planning and preparation that non-TDP students would not. Research Design: In fall 2011, a randomized group of ninth graders (class of 2015) were notified of TDP’s US$12,000 promise scholarship and their promise scholarship eligibility if merit requirements (e.g., 2.5 grade point average [GPA], 90% attendance) were met; a control group of ninth graders were not eligible. As the class of 2015 reached their senior year of high school, we interviewed a subset of TDP and non-TDP students to explore their perceptions of their senior year experiences. Using social capital theory, promise program research, and college access literature, we explored their perceptions, including the extent to which between-school and within-school inequities shaped the norms and resources received and used toward scholarship eligibility and their postsecondary goals. Findings: Study findings unpack how TDP students and non-TDP students navigate schools that are rife with both historical and contemporary inequitable arrangements that influence senior year course-taking, supplemental programming, and postsecondary advising—even for those students who were promised money for college in ninth grade. Study findings also unpack how TDP students’ access to supportive mechanisms and networks of support were uneven, even within the same school, which particularly affected students who needed the most support to meet their postsecondary aims and TDP scholarship requirements. Conclusion: Although the TDP scholarship was made available to students in their ninth-grade year, mechanisms and networks of support were not universally available and timely enough to disrupt the layers of inequalities within TDP schools and between high schools. Recommendations include disrupting existing inequitable arrangements and offering a more layered, systematic approach to introducing college-related information (personalized, hands-on guidance and support beyond scholarship messaging).