Taking up Gillian Rose’s observation that the pervasiveness of digital technologies in the realm of visual culture is not yet matched by digital methods of analysis, this chapter makes a case for the continuing relevance of approaches grounded in auto/biography studies, visual culture studies, and feminist media studies to studying visual autobiography in the digital era. It offers a set of critical reflections on the process of engaging responsibly with digital self-portraiture artefacts and archives, especially selfies, and highlights the inventiveness and critical reflexivity demanded by scholarly work on a particular form of convergence: the relationship between artists’ projects and their social media presence, including the solicitation of user participation in art installations and performance works.