As health care continues to evolve, the need for more effective health care transition (HCT) for all youth, but particularly children with chronic conditions and special health care needs, becomes even more important. With more than 90% of adolescents with chronic medical conditions now surviving into adulthood, suboptimal transition can lead to poorer quality of life and less successful adulthood.Through a series of clinical vignettes, the challenges of HCT are presented herein and accompanied by comments that underscore how these adolescents can best be helped to transition to successful adulthood. Several methods are presented to assess the readiness of adolescents and young adults (AYA) for transition. The process of transition can be divided into 3 stages: 1) setting the stage: initiation of HCT services and transition readiness assessment, 2) moving forward: ongoing provision of HCT services, and 3) reaching the goal: transfer of care and transition to adulthood.Several valuable suggestions for incorporating the HCT process into the health care system and improving HCT programs through a quality improvement (QI) approach are outlined. Future challenges in HCT include developing more precise assessments of transition status or transition readiness, better understanding the status and specific needs of AYA with chronic health care needs, continued program evaluation and QI efforts, and more reliance on patients and families to teach us about the challenges and methods in HCT that most effectively work for them.