Engaging students in service learning projects grounded in community psychology values and practices when working in a rural, conservative area provides several challenges and opportunities for faculty members. The authors share processes and outcomes from three case examples taking place between 2010 and 2013: (1) running focus groups and survey development with a local YMCA branch that predominantly serves people of color in low income housing, (2) the development of a strategic plan for the implementation of an art crawl in the local downtown community, and (3) the development and execution of an asset map evaluating supportive resources and spaces available to the local LGBTQA community. The authors reflect on feedback from students and community partners. These case examples highlight the complexity of balancing students’ skillsets, work and other life obligations, and desire to use classroom knowledge in community settings. It also highlights the importance of preparing community partners for working on applied research. We provide recommendations based on each project’s challenges and successes for universities and communities of similar demographics. Working in rural, conservative settings provide their own challenges and opportunities, but are well worth it if implemented in an intentional way, and more research is needed to strengthen our understanding of how best to engage students from a variety of social and political backgrounds.