This article describes the development of a service-learning project and analysis of student pharmacists’ participation therein. Using a mixed-methods approach, this study analyzed student pharmacists’ knowledge and attitudes after volunteering in the inaugural Medicare Outreach Program, a collaboration between the School of Pharmacy and State Health Insurance Assistance Program (SHIP) in which certified student pharmacists assisted Medicare beneficiaries with Part D plan evaluation and selection. Although results did not show a statistically significant difference in knowledge gained by students who volunteered (n = 71) compared to those who did not (n = 72; p = 0.57), thematic analysis of volunteering students’ reflections did reveal that they found their volunteering efforts to be meaningful learning experiences. Six major themes were identified overall showing that the program, which was designed to benefit SHIP and the community, also had a positive impact on students’ attitudes. Accordingly, the program’s sustainability plan is also discussed.