Teaching the ethics of image-taking, using, and preserving is always challenging, but for me, voices like those of Heider, Ruby, Gross, Katz, and Rouch were adequate enough sources of inspiration until my visual courses began to fill with Millennials. What is informed consent when the investigator is a member of the first generation to come of age with MySpace, Facebook, Twitter, Instagram, and Tumblr? Should all possible uses of photos and video taken in the field be covered in the document interlocutors are asked to sign? Are any just taken for granted in this age of ubiquitous visual documentation of everyday life? When do participation and the ensuing friendships that the best fieldwork fosters change the rules? While mentoring young anthropologists through first fieldwork experiences, these ethical concerns have taken on a different spin. A variety of Cloud-based tools for communication and project development have proven useful, especially Dropbox and Google Drive. Uploading project imagery to Instagram, Facebook, Tumblr, and blogs immediately raised issues of accessibility, privacy, permissions, informed consent, and long-term implications to me in ways that seemed quite distinct from those of my students. Discussion of these concerns with students of the Millennial generation forms the basis for my assessment of the possibilities and perils of image-management with today’s Cloud-based systems.