Troubling partnerships between the New York City Police Department (NYPD) and criminal informants during the mid-1920s adversely impacted urban African American women’s daily lives. Part of multiple hierarchies of municipal corruption, undercover surveillance operations represented one of many apparatuses law enforcers employed to criminalize black women’s ordinary behavior, to reinforce Progressive era images of black female criminality and promiscuity, and to deny women of their personhood and civil rights. Black New Yorker and criminal informant Charles Dancy, identified by local black newspapers as a vicious con artist and serial rapist, figured prominently in undercover police operations. Dancy falsely identified black women as sex workers and had them arrested, and in the process sexually assaulted women. New York blacks were outraged by some NYPD members’ use of informants as well as black women’s erroneous legal confinement. Situating informant work within the context of police brutality, racial inequity, and the denial of American citizenship, New York African American race leaders, newspaper editors, and ordinary folks devised and took part in resistance strategies that contested police surveillance operations and spoke on behalf of those who were subjected to state sanctioned violence.