The COVID-19 pandemic upended college education and the experiences of students due to the rapid and uneven shift to online learning. This study examined the experiences of students with disabilities with online learning, with a consideration of surrounding stressors such as financial pressures. In a mixed method approach, we compared 28 undergraduate students with disabilities (including mental health concerns) to their peers during 2020, to assess differences and similarities in their educational concerns, stress levels, and COVID-19-related adversities. We found that students with disabilities entered the Spring quarter of 2020 with significantly higher concerns about classes going online, and reported more recent negative life events than other students. These differences between the two groups diminished 3 months later with the exception of recent negative life events. For a fuller understanding of students’ experiences, we conducted qualitative analysis of open-ended interviews. We examined both positive and negative experiences with online learning among students with disabilities and mental health concerns. We describe how online learning enabled greater access—e.g., reducing the need for travel to campus—alongside ways in which online learning impeded academic engagement—e.g., reducing interpersonal interaction. We highlight a need for learning systems to meet the diverse and dynamic needs of students with disabilities.