Beyond the work of policy and platform analysis, this chapter examines some of the Wikipedia community’s struggles in inclusivity and representation. The encyclopedia community has actually been quite good at acknowledging challenges related to systemic social biases related to gender and race and its reliance on print-centric epistemologies. Researchers have also examined how harassment of women and trans-identified editors is normalized in the community. Marginalized (gender) identities often take on extra emotional and identity-related labor in order to navigate the spaces to productively contribute to the community. Tracing these issues will help to foreground the contemporary work and promise of the “sum of all human knowledge” and how Wikipedia puts that concept into practice with its community.