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 the institutional context. Data collected from 378 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, the 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.