Residence hall directors function as first responders during times of on-campus residential crisis and also train resident assistants on crisis procedures. These directors are often relied upon to serve as intermediaries for residential students when they are impeded by long wait times to see someone in campus counseling services. In addition, they work directly with resident assistants, some of whom experience suicidal ideation and need immediate support. This qualitative study explored how supervising suicidal resident assistants shaped the career planning and attrition of residence hall directors. A basic qualitative research design was used to better understand how residence hall directors made sense of their experience. This study captured the unique experiences of six current and four former directors in one higher education institution in the United States, some of whom confirmed their career path and some of whom changed direction following the experience. Implications for practice include having a supportive and competent supervisor, offering counseling sessions for these directors, and helping them create appropriate boundaries between their personal and professional lives. [The discussion questions at the close of this article were developed by Stacey Garrett.]