Undermatching, or students attending less selective colleges than they are academically qualified to attend, is seen as a contributing factor to the lagging college completion rate of low-income and first-generation college students. Addressing the mismatch has been mainly limited to the individual level. Through analysis of interview and longitudinal school administrative data with aspiring first-generation college low-income Latinx youth who started preparing to attend college in middle school, we find that the need to work, which students started doing in high school, was a major factor in students' undermatching. We show how employment collides with the structure of colleges as racialized organizations (Ray, 2019), especially matching colleges with high graduation rates. Selective colleges did not provide the support students needed to address their financial situations, and students attending schools to which they undermatched required more assistance navigating work and schools to stop them from dropping out. We also discuss program and policy solutions to address the low college completion rates of Latinx first-generation college students more fully as well as how to better support their need to work.