What explains variation in insurgent targeting of women within a conflict? What explains variation in insurgent targeting of women by insurgents of the same ideology between conflicts? This project examines the puzzle of inconsistency in rebel group targeting of women during insurgency operations. Using qualitative methods including comparative case selection, process tracing, and collecting novel data from original interviews I conducted, I find that targeting women can be a means of undermining and extracting concessions from the counterinsurgent, but that the efficacy of this strategy varies depending on the type of actor carrying out the counterinsurgency. Specifically, domestic counterinsurgents are more likely to be undermined by sex-selective targeting than are the other two types of actors I consider: foreign counterinsurgents or regional counterinsurgents. In addition, if targeting women is a means of undermining the counterinsurgent, I argue it operates through three mechanisms: (1) preventing information sharing between civilians and counterinsurgents; (2) emasculating male counterinsurgents for failing to protect "innocent" civilians; and (3) using violence against women as a bargaining tool to extract concessions from the counterinsurgent.