The need for improved care in U.S. nursing homes continues, and the role of RN delegation in nursing home quality is an area of ongoing interest. Nursing home RNs routinely lead nursing teams, with licensed practical/vocational nurses and unlicensed nursing personnel providing the majority of direct nursing care. Effective RN delegation of nursing activities is an essential component of nursing home care; yet, evidence suggests gaps in delegation practices, with implications for the quality of care. Directors of Nursing (DONs) are in key leadership positions to address gaps in delegation practices; however, few resources are available to guide DONs in this regard. As part of larger study to develop and test a delegation resource for DONs, this paper describes challenges DONs face in addressing gaps in RN delegation practices by the nursing staff under their charge. Using a descriptive qualitative approach, audio-taped semi-structured interviews were conducted with a convenience sample of 28 current/previous DONs and nursing home leaders. Thematic analysis was used to analyze the interview transcripts, revealing two key themes. First, DONs are commonly unprepared for the demands they face in this leadership position, in general and specific to RN delegation. Second, perceived and actual resource limitations in the DON’s work environment (i.e., staffing, time) challenge their capacity to ensure effective and safe RN delegation practices. These findings provide directions for further research to understand and address the challenges faced by DONs as the nursing home leaders charged with ensuring effective and safe nursing practice and improved resident outcomes.