The purpose of this article is to describe and explain a mentoring initiative for supporting and retaining middle school teachers. First, we examine the persistent problem of teacher retention in U.S. schools, particularly in middle schools. Then, we describe a mentoring initiative--a community practice mentoring model that is well-suited for facilitating professional learning and addressing the retention issue. We define community of practice and note how communities of practices work in schools. We argue that a community of practice model is both a powerful conceptual framework for mentoring teachers and a practical approach to supporting middle school teachers' practice. Next, we report on middle school conditions including organizational structures, effective professional learning, and the multigenerational nature of the teaching force. Subsequently, we focus on the key features of a community that enhances teachers' professional learning, reduces teacher isolation, and influences teacher retention. We end with our recommendations and a few concluding remarks about the importance of good talk and setting the conditions for teacher optimism.