Background Promise programs are a quickly spreading policy tool in the free college movement. Despite their rapid spread, promise programs remain generally untested and there is even less information about how they are implemented. Research Questions (1) In what ways were The Degree Project's (TDP) theory of change and intents represented in messaging materials to students and to school staff? 1(a) In what ways did these messages shape conditions (or not) for sensemaking? (2) In what ways did these messages support (or not) students and school staff in changing their practice? (2a) What changes in practice did we see (or not) for students and school staff? Intervention TDP, which was implemented in Milwaukee Public Schools between 2011–15, is the nation's first randomized control trial of a promise program. Freshmen in the treatment group were offered $12,000 for college if they met particular requirements (e.g., average 2.5 GPA, 90% attendance). TDP leaned heavily on marketing materials and personalized letters to students, families, and school staff to communicate its requirements and to provide college access tips. Research Design We analyze messaging materials, climate and exit survey data, and student and school staff interviews to understand how TDP's theory of change and intents were packaged into messaging materials and ultimately enacted among target students and staff. Findings TDP implementation was successful to a point. School staff handed out messaging materials; students understood the requirements and demonstrated an increase in motivation and desire to go to college. However, TDP failed to meet its goal of sending more students to college. Expectations for school staff (hand out flyers and speak to students) versus students were misaligned, contributing to a lack of substantive conversation and structures for students to convert their increased motivation to go to college into actionable practices over time. School staff were already stretched thin and, with no added structural support, were unable to interact more meaningfully with students. Conclusion TDP failed to send more students to college because it targeted change at the individual rather than organizational level. Students exhibited change in their motivation to attend college, but this was not met with the support needed to convert this motivation to meaningful action. To achieve their full potential, such programs will have to not only address financial barriers, but also leverage broader structural supports in schools to help channel increased student motivation in more productive directions.