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This article describes lessons learned about grouping by teachers and teacher educators who worked collaboratively to design and deliver a summer writing institute for a heterogeneous population of students about to begin ninth grade at an urban high school. Institute staff used co–teaching (Cook & Friend, 1995) extensively to provide support for student learners as well as to encourage professional learning about teaching writing. Such co-teaching allowed teachers to model expectations for academic tasks and behavior explicitly, create student groups that drew on multiple perspectives, approach teacher–student writing conferences deliberately, and provide extra scaffolding to youth in need of it. The article concludes with suggestions for applying the author team’s insights about grouping and co–teaching to more traditionally organized literacy instruction during the academic year.