Parents of youth with chronic health conditions encounter numerous challenges in supporting their children across pediatric treatment contexts. Structural barriers to care, such as access issues and coordinating care across school, health, and family settings, can exacerbate challenges to daily functioning. Parents are often concomitantly managing their child’s chronic condition, their own health care needs, work and family demands. For these parents, accomplishing a manageable “work-life balance” feels elusive, if not impossible, when a chronic health condition is part of family life. Based on a recent symposium presentation, combined perspectives from the disciplines of pediatric psychology, parenting, and human development and family studies consider key challenges and opportunities to assist parent coping with stress associated with caregiving amidst pervasive changes in healthcare service delivery. Two innovative interventions to support parents in both an outpatient (“Parents as Coping Coaches”) and an inpatient (“Putting Parents FIRST”) context are described, with commonalities and unique aspects highlighted for each. These programs are considered in reference to a rapidly changing healthcare landscape, growing focus on the family as a core context for care, and importance of parent/caregiver self-care and crucial role in supporting children’s long-term health and resiliency.