Since 2005, journalism has experienced a series of seismic changes due to economic factors, technological changes, and shifting priorities and news values. Photojournalism has been particularly affected by technology and business model changes, leading more outlets to rely on often geographically remote freelancers at the expense of dedicated photo staffs. These remote working environments and the mediated communication they necessitate have profound impacts for photojournalists’ development, roles, and responsibilities. Through in-depth interviews with photo editors and freelancers at top media outlets in the United States and guided by professional socialization, mentoring, and learning theories, this study explores what happens when the photojournalist–editor relationship is strained, mediated, or severed. It also seeks to examine what impact mediated interactions have on photographers’ learning and the quality of the media they produce. The findings reveal that the post-digital freelance model is more linear than the hierarchical staffer model and has a positive influence on workforce diversity, albeit at the expense of freelancers’ professional development and their opportunities to receive feedback from editors.