Family life is altered irrevocably when a young parent is diagnosed with or dies from cancer. This article tracks the genesis and transformation of a comprehensive psychoeducational support and bereavement program for children, adolescents, and parents affected by cancer. From the inception of the program, families with parents in active treatment participated in time-limited support groups. When a parent died, families transitioned out of support and into bereavement groups. As the cancer experience became more chronic, families remained in these respective groups for longer periods of time. This required clinicians to reconsider group structure to avoid the additional losses incurred as newly bereaved families transitioned from one group to another. Restructuring the program allowed participants to remain in familiar environments and to experience greater support and continuity in their care. Children, teens, and parents made clinical gains in communicating their needs and feelings to loved ones. Further, children and teens stayed on track developmentally, academically, and socially. Clinicians structuring these programs must be skilled in working simultaneously in both support and bereavement modalities. Recommendations for self-care and supervision are suggested.