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Undermatching, or students attending less selective colleges than they are academically eligible to attend, is seen as a contributing factor to the low college completion rate of low-income and first-generation college students. Economists have focused the issue on a lack of understanding by students of how financial aid works at selective colleges with high graduation rates and worked to help high-achieving low-income students with information gaps. In this paper, we show that such explanations fail to reveal the full context of students’ lives. Using interview and school administrative data with would-be first-generation college, low-income students who started preparing for college in middle-school, we show how family economic circumstances influenced college choice. We also detail program and policy solutions to more fully address the issue of low college completion rates of students from low-income families.