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The COVID-19 pandemic has presented unique challenges and stressors that are testing the resilience of residential life staff in significant ways. Like many colleges and universities, this campus of study provided almost exclusively remote instruction during the 2020-21 academic year while providing housing for approximately 30% of the undergraduate population. In 2021-22, this campus was near the residential capacity while providing mostly in-person instruction. Even with a 97% vaccination rate for students, monitoring the safety and wellness of residents created unique stressors for both professional and paraprofessional staff. The varied impacts of the pandemic brought constant change, and the results of such change were no more apparent than in the 24/7 environments of the residential community. This article explores the depth and breadth of issues related to the stress, coping, and resilience of live-in student staff and identifies variables that contributed to their well-being. Using a mixed methods approach, a comparison was made between student hall staff and the rest of the campus population on self-reported mental health concerns. These data were used to create changes in practice to improve the paraprofessional experience, such as professional staff assuming more in-person responsibilities and making mental health support more readily accessible to paraprofessional staff. [Discussion questions developed by Zakery Earp.]