In the field of adolescent literacy studies, writing has been neglected in both research and instruction (Juzwik, Curcic, Wolbers, Moxley, Dimling, & Shankland, 2005; Graham & Perin, 2007; Scherff & Piazza, 2005; Troia, 2007), especially in urban settings. Given the importance of writing instruction in secondary education, this qualitative case study investigates the writing experiences of five urban adolescent writers in a high school in a major city in the Southeastern U.S. Research questions included: (1) What are the writing experiences of urban adolescents in and out of school? and (2) In what ways do urban adolescents make use of multiliteracies in their writing experiences? This multicase study (Merriam, 1998; Stake, 1995) includes data collected from interviews, observations, field notes, samples of student work, and electronic messages. For a period of six months, five key participants acted as co-researchers by providing feedback and collaborating on inductive analysis of the data. Findings revealed that students employed multiple modes and genres of writing, and that they viewed social and technological contexts as important factors in their composing experiences. Despite these findings, the students did not have many opportunities to take advantage of recent advancements in 21st century writing approaches. The new ―Age of Composition‖ (Yancey, 2009) has not arrived in urban environments where concerns of power and access remain. This study contributes to the field of literacy studies by illuminating the experiences of the participants and providing recommendations for educators in urban contexts. As Yancey recommends, educators need to design a new model for 21st century composition instruction. The findings of this study suggest the following instructional implications for secondary classrooms: 1. 21st century composition instruction should include multimodal compositions and multimedia projects. 2. 21st century composition instruction should give a central role to the use of technology. 3. Students should have opportunities for personal expression and identity exploration. 4. Teachers should create composition lessons that engage and empower students. 5. 21st century composition instruction should be transformative.