Writing instruction is a particular challenge because there is no singular, linear solution to teaching students to write well. This book approaches writing as a wicked problem that takes place in complicated contexts. Through both scholarly research and teacher reflection, it examines ELA classrooms and the experiences of writing teachers to identify approaches that have proven effective with adolescents. The book uses wickedity to frame the problems of teaching writing and offers context-specific solutions enacted by teachers. While it addresses the realities of standardized ways of teaching and assessing writing, the book also highlights the deep professional knowledge and practical strategies teachers bring to writing instruction in middle and high school classrooms. Chapters grapple with tensions between testing and authenticity, assessing writing in nuanced ways, and finding enjoyment in the work of teaching writing amid and alongside persistent complexities. Specific topics include students' writing process, revision, students as decision makers, multimodal writing, assessment and writer's notebooks, data-driven instruction, the high school–to-college transition, and teacher professional development.