Community service-learning (CSL) is commonly featured in health promotion curriculum. Lauded for its pedagogical richness and transformative potential, CSL is also pedagogically messy and often experienced as a struggle. And yet, the content, contexts and conditions of that which students find disorienting in CSL have garnered little attention in the literature. In this qualitative, phenomenological study, we explore the “disorienting dilemma” as an understated concept in CSL. Our aim is to better understand the disorienting dilemma to “make CSL a smoother experience for everyone.” We draw upon reflections from 39 students enrolled in a full-year undergraduate health promotion CSL course. Using directed content analysis, we read and coded 390 reflections. In mapping the codes ( n = 2104), we found them to cluster around three domains: (i) aspects of the CSL learning experience that were most disorienting, (ii) course aspects that enabled students to navigate their disorientation, and (iii) how students relate their learning to the disorientation. Students often shared their emotional experience of CSL as a pedagogy, and that they struggled with the process of real program planning, and uncertainty with how they related to the community. Often, it was the practical, social, and relational content that students struggled with that morphed into support for students to navigate their disorientation. We found students to relate their disorientation to new self-learning, a changed and more collectivist criteria of success, and an altered sense of self in relation to community. We discuss theoretical and pedagogical implications of the disorienting dilemma.