Sustainability in community engagement projects depends on careful attention to the ways we navigate complex, often challenging relationships with our partners, our students, agencies, and the institutions in which we occupy multiple, sometimes competing roles. This article considers the difficulty inherent in developing and maintaining relationships with the community members who choose to participate in our research. Based on the experiences of three undergraduate students in a community literacy seminar, the author traces the ways these students confront challenges in their projects, arguing for the value of difficulty in community literacy work.