The Opportunity Youth Healthcare Pipeline (OYHP) initiative, a collaborative effort by J.P. Morgan Chase, United Way of Greater Houston, Memorial Hermann Health System, and several community-based organizations, seeks to connect youth with career opportunities in the health care sector in the Houston region. In partnership with the United Way, the Kinder Institute for Urban Research conducted an in-depth study to explore the operational dynamics, challenges, opportunities, and successes of the implementation of the program. Drawing on insights from participants, program staff, and stakeholders, the study highlights the need for enhanced program awareness, clearer communication channels, tailored support initiatives to better serve Opportunity Youth (OY), and training programs that meet the evolving needs and expectations of the job market.