A middle school language arts teacher reflects on his experience in utilizing a school-housed online social network to create avenues for authentic audience, purpose, and response to student writing. With many technology proponents advocating a 21st century education, the fact that interacting with the Web 2.0 environment is essentially a reading and writing exercise is too often ignored. Drawing on the work of Wiggins and Sommers, this article examines how effective writing concepts might be translated into the new online tools that make composing and publishing seamless and immediate.