Last year, the author and his ninth-grade students explored ways to use mobile media devices such as iPods and cell phones to help guide literacy practices in their English classroom. Their school, South Central High School (SCHS; a pseudonym), is a public high school located in urban Los Angeles. As part of their seven-week exploration, the author had selected Cory Doctorow's 2008 young adult novel "Little Brother" as a text they would read as a class. The novel has a flexible Creative Commons license, so in addition to providing his students with paper copies of the novel, he also gave them PDFs and an audiobook on their iPods. Though several students elected to read paper copies at home, many students chose to engage with the text through the digital versions in class. Throughout the class, the biggest challenge with using these digital devices for "English stuff," as his students called it, was not the fears of distraction that are often pointed to as reasons for not incorporating mobile media devices in schools. Instead, the biggest challenge was identifying and understanding the changing context of reading, writing, and producing as a result of advances in technology. In this article, the author shares an example of engagement in the class that best highlights the challenges that educators face in teaching with the tools of a wireless, digital generation.