Caring for patients with cancer is highly stimulating and rewarding, attracting health professionals to the field who enjoy the challenge of managing a complex illness. Health professionals often form close bonds with their patients as they confront ongoing disease or treatment impacts, which may be associated with multiple losses involving function and/or eventual loss of life. Ongoing exposure to patient loss, along with a challenging work setting, may pose significant stress and impact health professionals’ well-being. The prevalence rates of burnout and compassion fatigue (CF) are significant, yet health professionals have little knowledge on these topics. A 6-week continuing education program consisting of weekly small-group video-conferencing sessions, case-based learning, and an online community of practice was delivered to health care providers providing oncology care. Program content included personal, organization and team-related risk and protective factors associated with CF, grief models, and strategies to mitigate against CF. Content analysis was completed as part of the program evaluation. In total, 189 participants (93% nurses) completed the program, which was associated with significant improvements in confidence and knowledge of CF and strategies to support self and team resilience. Qualitative themes and vignettes from experiences with the program are presented. Key themes included knowledge gaps, a lack of support related to CF and strategies to support resilience, organization- and team-based factors that can inhibit expression about the impacts of clinical work, the health professional as a “person” in caregiving, and the role of personal variables, self-skill practices, and recommendations for education and support for self and teams.