This article explores the labor of contemporary digital privacy advocates and their myriad efforts to protect and preserve public interests during the era of Big Tech companies. It is based on qualitative interviews with professional staff, lawyers, and policy analysts at multiple major advocacy organizations in Washington, DC. We have employed a grounded theory approach to address four labor-related themes that consistently emerged across our interviews: coalition building, agenda formulation, the art of navigating public- and private-sector relationships, and balancing a domestic and global policy landscape. In the current policy landscape, there is an intensifying degree of advocacy–industry coordination taking place, in part because of US regulatory roll-backs under the Trump administration and a gridlocked Congress. As a result, advocacy organization staff members often rely on companies for information to do their assessment and agenda-setting work. They also apply pressure to these companies and force them to think about how their technologies and operations impact users and publics around the world; they mount legal challenges to various media and tech initiatives to ensure public interests are protected; and some end up working with or for these companies in ways that may impart and integrate the values of advocacy organizations within profit-driven organizations. This article explores the multiple dimensions of advocacy labor which itself is often excluded from media policy and industry analysis.