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This paper studies the 2011-15 implementation of a promise scholarship entitled The Degree Project (TDP) in Milwaukee Public Schools. TDP aimed to promote college-going behavior in students while stimulating school staff to interact more with students around college access. Despite faithful implementation, TDP did not achieve its desired outcomes. We draw on complementary bodies of literature that outline the role of collective sensemaking in the enactment of policy messages to provide insight into TDP’s results. We analyze student and school staff interview data and TDP’s messaging materials to answer the questions: In what ways were TDP’s theory of change and intents represented in messaging materials? How did school staff and students make sense of these messages? How did the interaction between the messaging and how it was understood shape the implementation and effects of the intervention? We demonstrate that the degree of change in practice – the “ask” – that TDP hoped for differed greatly between students and school staff. Our analysis delineates this difference in practice expectations and provides insight into how the intervention design could have better supported students in their college access journey.