This study explores the extent to which college context (two- vs. four-year), gender, and race/ethnicity correlated with worsening course outcomes during emergency remote teaching during the COVID-19 pandemic, by comparing outcomes within students between the fall 2019 pre-pandemic and spring 2020 pandemic terms. In particular, it explores the extent to which prior voluntary online course-taking is related to patterns among these groups. Results from this study suggest that students at two-year colleges, men, and Black and Hispanic students had worse outcomes during emergency remote teaching, if they had not previously voluntarily enrolled in online courses. However, these differential trends were not observed among students who had voluntarily enrolled in online courses prior to the pandemic.