Student engagement in the classroom is important for academic and future success. Many students with disabilities rely on classroom supports, such as assistive technology (AT), to access the curriculum and demonstrate their understanding. The COVID-19 pandemic forced many school districts to abruptly shift to emergency remote instruction. Numerous factors impacted the individual student experience and their classroom engagement. As engagement is vital for student success and well-being, this study aimed to gain a rich understanding of the student and caregiver experience during emergency remote instruction. Nine dyad pairs of AT student users with disabilities and their caregivers participated in semi-structured interviews. Using Interpretive Phenomenological Analysis (IPA), four superordinate themes were constructed to reflect participant responses. During emergency remote instruction, daily student occupations changed. Students reported feeling socially isolated and confused by the added school demands from the home environment and caregivers, and schoolwork was less meaningful. Students were forced to redefine what it meant to be a student. Future research should continue to use IPA methodology to generate a richer understanding of the student experience and to explore long term impact of emergency remote instruction on occupational participation.