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Postsecondary institutions have designed a wide range of approaches to support students from low-income backgrounds, yet financial stressors still have a significant impact on students’ experiences. This paper seeks to enhance understanding of how low-income students navigate financial stress by integrating the asset-based concept of financial well-being and including a focus on institutional context. Data collected from 160 interviews with students from low-income backgrounds illustrate complex ways that students experience financial stress and financial well-being. By centering students’ perspectives in analysis while also accounting for programmatic and institutional contexts, authors aim to push theory and practice toward a more nuanced understanding of how to best support students from low-income backgrounds as they navigate affording college and fostering financial well-being.