The widespread use of social media (e.g., Facebook, Twitter, YouTube) has led many researchers and practitioners to explore their benefits for education, including their ability to connect people together in ways that value diverse perspectives, creativity, and individual expression. However, there are some complex cultural and social aspects of these tools that deserve attention and that educators and students should be aware of. In this chapter, we explore a variety of issues through the themes of (1) literacy, (2) privacy, (3) civility, and (4) identity. Literacy issues include digital participation divides and the ways that differences in abilities among students to use these tools lead to inequities in educational and social opportunities. Privacy issues include those involving the sharing of personal information via ubiquitous, persistent technologies and the subsequent hierarchical and lateral surveillance that this enables. Civility issues include cyberbullying and other utilizations of these media to manipulate the emotional states and social standing of others through dehumanization, decontextualization, and persistent abuse. And identity issues include those arising from the incomplete, skewed, or performative expression of identity via social media and subsequent tensions that arise between the use of acceptable identity fragments and the reductionism that occurs as authentic identity is translated into online spaces. With each of these themes, we explore pertinent problems that arise in social media (e.g., echo chambers, incivility, identity collapse) and also provide suggestions for educators to alleviate their severity.