The purpose of this study was to investigate the challenges teachers of students with disabilities and extensive support needs experienced during the COVID-19 pandemic. Nine educators who taught in a public school district during the 2020 pandemic engaged in interviews at three points of time, when: (a) schools closed in March, (b) during summer break, and (c) when schools reopened in September. Participants described the challenges they faced transitioning to online instruction and back to face-to-face instruction, including: (a) failing to equip students with technology skills, (b) difficulty adapting instructional techniques, (c) inability to access student materials and resources, (d) discomfort with temporary IEPs, (e) dependency on families "acting as a paraprofessional," and (f) safety and logistical barriers. Administrative support, or the lack thereof, underpinned all discussions. Implications for practice and research are discussed.