The journey to adulthood is complex and multi-dimensional. Young people may be independent in some spheres of their lives, but dependent in others. For young people with a disability, long-term condition, or mental health problem there are additional hurdles. As they move between health and social care services, they will find significant differences in expectations, delivery, and culture. At the same time, their own needs will be evolving. Despite a great deal of guidance on effective transition support, in 2014, England's Care Quality Commission highlighted a shortfall between policy and practice. The result is confusion and frustration for young people, their families, and the staff caring for them. Seamless transition to adult services is by no means a universal experience. Here the authors offer two case studies that triangulate inter-related perspectives: those of young people, parents and carers, and the professionals involved in successful models of transition support. The case studies illustrate how the challenge of transitioning to adult services is actually experienced and how, despite some concerns held by young people, parents, and carers, well-planned and coordinated transitions can have positive outcomes for the families involved