This article describes a writing partnership that involved university preservice teachers and ninth grade students enrolled in an integrated social studies/language arts class. While the high school students found the experience exciting and satisfying, the preservice teachers expressed anxieties and concerns as they endeavored to foster academic literacies. We conclude with reflections on the challenges of preparing a new generation of English educators to teach writing in rich and meaningful ways where they have not themselves benefited from such experiences in their own "apprenticeships of observation." (Contains 2 notes.)