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Students experiencing homelessness spend their nights in various settings, including shelters, with friends/families (doubled-up), motels/hotels, and unsheltered contexts. Yet there is limited quantitative research on how educational outcomes vary by residential context. We analyze data from over 400,000 students in Houston Independent School District from 2012–2013 to 2016–2017 via fixed-effects models and coarsened exact matching techniques. We find that students who became homeless attended less school and were more likely to drop out than nonhomeless students but had comparable achievement growth and disciplinary infractions. However, outcomes varied significantly by residential context: Doubled-up students fared relatively well on most outcomes, whereas students in shelter had particularly poor attainment. Results highlight the importance of research and practice that attends to differences by residential context.