This article investigates the creation of an online photo database at the Lesbian Herstory Archives (LHA). The status of images of sexuality in this collection presents opportunities for reflecting on the cultural politics of digitization in community archives, including the accessibility of sexual materials in lesbian, gay, bisexual, and transgender (LGBT) archives as they move online. I argue that the design of this project has generated moments of reckoning with various political contexts in which the archives moves. The LHA's approach to digitization is improvisational, open to revision and critique, and willfully imperfect in its management of considerations such as metadata. Digitization presents the archives with the opportunity to consider the ways that the historical representations of sexuality it houses challenge the normative imperatives that can accompany digital media practices, including the ways that all kinds of sex practices and gendered ways of being scramble the categorical logics of structured databases.