Background: Grief and loss are common experiences for children and adolescents, particularly during the COVID-19 pandemic. Educators feel unprepared to support grieving students due to lack of training. We studied educator experiences receiving grief-sensitive training as part of the grief-sensitive schools initiative (GSSI), which provides grief-sensitive training, online video-based and print resources, and a financial grant to schools and school districts for use in supporting grieving students. Methods: Fourteen New York and Florida educators who received GSSI training participated in small focus groups or semi-structured interviews on their experiences receiving GSSI training and supporting grieving students during the pandemic. Transcripts were analyzed using grounded-theory analysis. Results: Emergent themes included increased confidence engaging grieving students, the desire for recurring trainings, the value of receiving training from an expert on pediatric grief and loss and the opportunity to ask questions, the need for grief-sensitive training to reflect the cultural diversity of school communities, the unique losses experienced by students during the pandemic, and compassion fatigue and burnout in educators. Implications for School Health Policy, Practice, and Equity: Policymakers should recognize the effects of grief on students' learning and development and collaborate with educators to develop resources. Conclusions: Educators found GSSI training useful in supporting grieving students, particularly during the pandemic.