For instructors engaged in teaching evaluation, bridging the gap between the content of formal educational experiences and what we want future evaluators to be able to do in practice remains a challenge. Studying the format and quality of university courses focused on program evaluation is one mechanism through which we might begin to narrow this gap. This article describes a community-engaged, project-based evaluation course that was taught during five semesters, and uses qualitative data to explore student experiences within the course along three dimensions: experiential education, interdisciplinary collaboration, and community partnerships. In particular, we highlight the productive yet uncomfortable role that challenge and ambiguity play in animating evaluation learning. We suggest implications for teaching evaluation based on our findings.