This article examines how faculty at one college respond to student writing, how students interpret that feedback, and how through collective self-evaluation and community-building workshops some faculty paved a path toward more productive response. The first part of the findings resonate with what scholars in the 1980s discovered: that teachers’ feedback strategies often operate at cross-purposes with students’ motivations and understandings. Asking why, after forty years of scholarship, such counterproductive strategies still prevail, the study suggests burdensome workloads, lack of training, rigid applications of rubrics and genres, and isolation from peers are to blame. It then profiles three teachers who, despite these obstacles, provide deep-reaching feedback. Although their pedagogies and backgrounds differ, they share common bonds, teaching authentically from who they are, an approach that is open to all teachers once they feel freed to adopt it.