Federal Work-Study (FWS) is a form of student employment in postsecondary education funded by a student's financial aid. At the University of South Florida (Tampa campus), in the Community-Based Federal Work-Study (CBFWS) program managed by the Office of Community Engagement and Partnerships (OCEP), there has been a decreasing rate of participation among its male students compared to female students. This study examined the experiences and perspectives of male students in CBFWS at USF. The study was guided by one central research question with three sub-questions: From the perspective of the male student participants, what is their CBFWS experience in relation to: (1) academic performance, (2) career readiness, and (3) social support? This study utilized an exploratory, qualitative case study approach theoretically framed by Albert Bandura's Social Cognitive Theory. The study utilized three sets of data: (a) documents, (b) interviews, and (c) a researcher journal. The findings showed most male students in CBFWS believed the program provided opportunities to build communication skills, network with other professionals, build relationships with staff members, and increase knowledge of the local community. The behavior and cognitive factors of the participants were particularly influenced by the environmental context of the individual community placements. Implications of the findings include striving to build a framework for CBFWS which considers the culturally universal and culturally specific qualities of its students. In turn, this could result in promoting greater engagement among male students in community-based programming. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]