Efforts to combat homelessness are hampered by perceptions involving negative stereotypes. One method to change perceptions is university-based cocurricular community service that gives students direct interactions with individuals experiencing homelessness and poverty. This qualitative study collected data with undergraduate volunteers working with individuals experiencing homelessness to determine the impact on perceptions of poverty and homelessness, knowledge, and skill development. Qualitative analyses revealed five key themes: (1) understanding homelessness/poverty, (2) understanding social welfare programs, (3) development of communication and leadership skills, (4) gaining financial literacy, and (5) self-knowledge. Results are discussed for practice, policy, and future research, including a pre/posttest design.