Through the Enrollment Outreach Grant Program, Massachusetts Medicaid provides grants to community organizations to use innovative strategies to reach uninsured residents and assist them with enrollment in Medicaid and other state subsidized health insurance options. UMass Medical School’s Center for Health Policy and Research evaluated the contribution of this program to advancing Massachusetts health care reform goals to increase the number of state residents with health insurance. The evaluation aim was to understand how the program has a) supported people with navigating health insurance enrollment, and b) adapted in scope and services to meet the unique needs of multiple stakeholders. Using a case study methodology, the evaluation team conducted site visits to a third of grantees (N=17) to interview outreach workers and supervisors and shadow outreach worker activities. This paper will present the project’s findings and highlight use of qualitative methods to understand how health care reform goals are achieved.#2010Conference #HealthEvaluation