Scholars and practitioners across domains are increasingly concerned with algorithmic transparency and opacity, interrogating the values and assumptions embedded in automated, black-boxed systems, particularly in user-generated content platforms. I report from an ethnography of infrastructure in Wikipedia to discuss an often understudied aspect of this topic: the local, contextual, learned expertise involved in participating in a highly automated social–technical environment. Today, the organizational culture of Wikipedia is deeply intertwined with various data-driven algorithmic systems, which Wikipedians rely on to help manage and govern the “anyone can edit” encyclopedia at a massive scale. These bots, scripts, tools, plugins, and dashboards make Wikipedia more efficient for those who know how to work with them, but like all organizational culture, newcomers must learn them if they want to fully participate. I illustrate how cultural and organizational expertise is enacted around algorithmic agents by discussing two autoethnographic vignettes, which relate my personal experience as a veteran in Wikipedia.