The purpose of this reflective essay is to encourage the discussion of community-engaged scholarship (CES) that does not progress as planned. Insufficient attention is given to lessons gleaned from missteps and outright failures experienced by scholars in the field, which results in a paucity of documented cases and recommendations for improvement. To address this gap in the literature, this article features vignettes from scholars in the field whose experiential wisdom may inform practice for individuals as well as institutional strategies. The authors discuss implications for practice informed by their experience in developing community-engaged scholars and the shared wisdom of the contributors whose experience and failures provide insight for emerging scholars. The essay concludes with recommendations for future research related to how we experience and learn from failure in CES.