["Child &Family Social Work, EarlyView. ", "\nABSTRACT\nTransition to adulthood is a developmental stage marked by multiple opportunities and challenges that have significant impacts on young people's well‐being. Young people involved in child welfare often encounter hardships during this transition and struggle to negotiate it successfully due to the adversities they experience before and during care. To address these challenges, two experienced out‐of‐home care (OOHC) parents collaborated with a community‐based child welfare organization to develop the Milestone Program—a web‐based application for care providers to strengthen their relationships with young people in OOHC and thereby support their readiness for adulthood as they approach the age of leaving care. This study was initiated by the community‐based child welfare organization who invited the research team to collaborate on evaluating the Milestone Program. Rooted in resilience principles, this study explored young person–caregiver relationships, young people's readiness for leaving care, caregivers' confidence in supporting the young person and satisfaction with the program among 17 young person–caregiver dyads over a period of 6 months. This study offers preliminary evidence for the potential of building skills to prepare for aging OOHC through meaningful connections with care providers. The value of research‐community collaboration in developing, implementing and evaluating transition services is highlighted.\n"]