This study examined the factors that contributed to students with disabilities' positive and challenging experiences transitioning to remote learning in the spring 2020 semester due to the COVID-19 pandemic at a small, two-year community college located in the Midwestern United States. The study administered a confidential survey to students with disabilities to learn about their positive and challenging experiences and concluded with an interview with the Vice President for Academic Affairs to gain additional insight into the college's timeline and transition procedures to remote learning. This study discovered both positive and challenging experiences with remote learning for students with disabilities. The positive experiences were comfort with the learning management software Blackboard, ease of access to grades, instructor helpfulness with accommodations, and images and video instructional materials utilized in their courses. The challenges discovered were related to faculty and peer communication, testing services, confidence with remote learning, and lack of knowledge about Student Accessibility Services. The data concluded that students diagnosed with a mental health disability were less aware of Student Accessibility Services than students with other disabilities. The recommendations outlined in this study will help higher education institutions, faculty, and student Accessibility Services Offices design effective approaches in supporting students with disabilities' accommodation needs when taking online courses.