Background: Promise scholarship 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. Focus of study: We study the implementation and effects of the nation's first randomized control trial of a promise program entitled The Degree Project (TDP). We focus on whether and how TDP's messaging materials helped educators and students think differently about, and potentially change, their college-going and college access-oriented practices. We draw on complementary bodies of literature that outline the role of policy messages in shaping conditions for sensemaking and implementation to challenge some of the core assumptions driving promise program design. Through a detailed analysis of messaging materials, survey data, and student and school staff interview data, we address the following research questions: (1) In what ways were TDP's 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?; and (2a) What changes in practice did we see (or not) for students and school staff? Intervention: TDP was implemented in Milwaukee Public Schools (MPS) from 2011-15. Thirty-six MPS high schools were paired on prior college-going rates and size, and one from each pair was selected to be a treatment school. All first-time freshmen in the treatment schools were offered $12,000 for study in a Wisconsin public or a private non-profit higher education institution if they met particular requirements (average 2.5 GPA, 90% attendance, on-time high school graduation, complete a Free Application for Federal Student Aid, attend a college in Wisconsin, begin college within 15 months of graduation). 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. TDP required school staff to hand these letter to students. They were also encouraged to remind students of their status and encourage them towards the goals of college. Research Design: We analyze three forms of data--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, disseminate, received, and, ultimately, if this supported change in practice for target students and school staff. We utilized three distinct forms of analysis. For the messaging materials, we conducted content coding on all documents and artifacts sent to students and school staff over the four-year implementation of TDP. We coded for ways the materials communicated ideas about the TDP intervention and, more broadly, ideas about the college access process. For the survey data, we identified the TDP-relevant questions and ran basic means and standard errors for these questions. Lastly, for the student and school staff interviews, we first conducted an iterative, inductive analysis of the data then further refined our categories based on the research questions. Findings: TDP implementation was successful up to a point. School staff handed out TDP messaging materials, students understood the requirements and demonstrated an increase in motivation and desire to go to college. However, despite these factors, TDP failed to meet its desired outcome of sending more students to college. We find that misalignment in expectations for school staff (hand out flyers and speak to students) vs. students (raise their GPAs and attendance) were misaligned, contributing to a lack of substantive conversation and structures for students to convert their increased motivation to go to college to actionable practices over time. In other words, TDP's model and messaging materials helped mobilize the interpretation part of the sensemaking process. Students were well aware of the scholarship and what it might mean for their college-going chances. Despite these factors, TDP failed to successfully translate students' increased motivations to increases in measurable outcomes (e.g., GPA). In other words, it failed to shape and maintain sufficient conditions for the sensemaking--such as fostering substantive, ongoing conversations--needed for students to reimagine their current practice and take effective action towards a new TDP-defined reality. Moreover, school staff were already stretched thin, and with no additional structural support (e.g., increased support for interacting with students), were not able to contribute to fostering the conditions for sensemaking that is necessary for a change in practice for students. Conclusion: We argue that TDP failed to send more students to college because it targeted change at the individual rather than organizational level. Consistent with that, messaging was targeted at individual action rather than broader system change. Students did exhibit change in their motivation to attend college, but this was not met with the structural support needed to change their current behaviors. When student-level shifts in meaning making are met with system-level supports, students are better able to convert motivation and knowledge to concrete reality. To achieve their full potential, such programs will have to not only address financial barriers, they will have to leverage broader structural supports in schools to help translate increased student motivation in more productive directions.