The increased use and accessibility of digital technologies is predicted to cause a fundamental shift in the way young people communicate, socialize, learn and create. If young people really are learning differently, educators will need to find new ways to appeal to students’ interests and engage them with course material. Digital Humanities initiatives with an emphasis on pedagogy, like the one at San Diego State University (SDSU), may be the answer to incorporating technology into the liberal arts classroom. Not only are these initiatives helping professors engage with students in new ways, but they are also teaching students how to use digital technologies critically and creatively. As multimodal and digital media become legitimate sources of knowledge and communication in education, students are no longer confined to reading from a textbook or traditional lectures. Now different and new forms of media (Web 2.0), such as social media, and student-created websites and blogs are incorporated into coursework. I explore the assumptions that go into transforming pedagogy at the university level to include digital media in undergraduate writing courses at SDSU. I take an ethnographic approach to investigating perceptions of the ways in which these forms of media are incorporated into Rhetoric of Written Arguments classes (RWS 100). In the Fall of 2016, I conducted in-class participant observation and in-depth interviews with students, instructors, and faculty. I also administered a questionnaire on student blog use. Additionally, I incorporated results from two of Dr. Chris Werry’s RWS 100 surveys on digital literacy. I specifically explore how these groups conceptualize digital literacy compared to traditional forms of literacy, and how their media ideologies affect their uses and reactions toward using Web 2.0 tools for educational outcomes. Among these three groups, I found there to be a wide range of experience, comfort levels, and ideologies surrounding the use of digital media. Not only does this diversity challenge the assumptions associated with the digital native/digital immigrant binary, but it also provides insights into how these transformations in pedagogy are being received and how to introduce and maintain initiatives, like the Digital Humanities Initiative at SDSU.