The COVID-19 pandemic decreased college enrollment and disrupted academic progress, particularly among disadvantaged students and institutions. Just before the start of the pandemic in spring 2020, 31,511 undergraduate students attending colleges of The City University of New York responded to a survey detailing their circumstances. Lasso regression followed by mixed-effects logistic regression modeling were used to identify predictors of (1) fall 2020 reenrollment, (2) associate's-degree graduation or transfer to a bachelor's-degree program by associate's-degree students by fall 2022, and (3) graduation with a bachelor's-degree by bachelor's-degree students by fall 2022. Part-time status, food insecurity, gender, and major predicted reenrollment and graduation or transfer. Belonging, friendships, and extracurricular involvement predicted fall 2020 reenrollment. Race/ethnicity and ASAP program involvement predicted associate's-degree graduation or transfer. These findings can assist institutions in targeting effective interventions for helping students faced with external challenges.