Understanding what happens when teachers embrace digital media for literacy learning is critical to realizing the potential of learning in the digital era. This article examines some of the ways that a high school teacher and his students leverage digital technologies for literacy learning in their humanities classrooms. The author introduces the concept of layering as essential not only to understanding the possibilities of digital media in classrooms but also to harnessing digital technologies for literacy learning. The article is organized around three key aspects--multiple texts, collaborative texts, and simultaneous texts--that are central to the author's conceptualization of layering. Whereas the near-constant stimulation and text density associated with learning environments that are saturated with digital media, networked devices, and always-on technologies are often understood as interferences to what is often considered "real" learning, the author argues that they are fundamental components of the learning environment.