The multidimensional role of entry-level, live-in residence life and housing staff has grown even more complex in recent years. These staff members, often referred to as resident directors, are frequently asked to go beyond the role of RA supervisor, community builder, and policy enforcer. Now they also serve to support students with significant mental health concerns, manage COVID-19 response protocols, and act as a vital conduit helping campus partners connect with students where they are most accessible--their residence on campus. This multi-site case study explored how departments support the well-being of their entry-level, live-in staff, recognizing significant changes in the role over the past few decades. Individual interviews were conducted with senior staff and live-in staff to understand their perception of the support being offered and received. Manning's organizational frames were used in the design of the study and informed data analysis and interpretation. Findings suggest that the increasing number of responsibilities, the demands of crisis response, and campus partners' misunderstanding of the role contribute to an overwhelming situation for entry-level, live-in staff. An investment in relationship building and compensation packages, including benefits such as pet and partner policies, can help to support staff's ability to care for themselves. Recommendations focus on how departmental leaders can address challenges that are contributing to staff exhaustion and burnout. [The discussion questions at the close of this article were developed by Brad Johnson.]