Nationally, there are low rates of high school-age youth receiving health care transition (HCT) preparation from health care providers. This pilot study implemented and assessed the use of a structured HCT process, the Six Core Elements of HCT, in two school-based health centers (SBHCs) in Washington, DC. The pilot study examined the feasibility of incorporating the Six Core Elements into routine care and identified self-care skill gaps among students. Quality improvement methods were used to customize, implement, and measure the Six Core Elements and HCT supports. After the pilot, both SBHCs demonstrated improvement in their implementation of the structured HCT process. More than half of the pilot participants reported not knowing how to find their doctor's phone number and not knowing what a referral is. These findings indicate the need for incorporating HCT supports into SBHCs to help students build self-care skills necessary for adulthood.