This paper discusses experiences incorporating social media into Middle East Studies classes in a liberal arts college context, with a particular focus on their intensive use in two courses offered repeatedly over the past several years: International Politics of the Middle East & North Africa; and Media & Politics in the Middle East & North Africa. The paper tracks the author’s refinement, through trial and error as well as the application of pedagogical theories, of how tools such as blogs, twitter, and social bookmarking can productively be designed into a syllabus as well as applied through adaptation and improvisation as courses run. A significant portion of the paper will be dedicated to discussing the educational value of student blogging, including how to design effective assignments that foster student engagement with the medium for both reflection and conversation. It will include examples of blog-based assignments that help students understand and narrow the gap betweeen their lives and experiences and those of Middle Easterners. Sections on twitter and social bookmarking will consider what works (and doesn’t) in overcoming student resistance to new tools, or tools used in new ways, as well as the effectiveness of modeling versus other approaches in teaching productive social media use in the context of learning about the Middle East and North Africa. A final section will weigh the costs and benefits of incorporating these tools, with a particular emphasis on necessary time commitments from instructors and students, proposing a rubric that can be applied in deciding whether to incorporate a particular tool, and how. The paper will conclude with an argument in favor of the considered application of social media tools to enhance the teaching of certain kinds of content and the transfer of certain skills, but cautions against any over-enthusiastic embrace of them. It also invites readers to use consideration of social media-based assignments as a way to reconsider the purposes and effectiveness of more traditional assignments.