This article draws on in-depth interviews with 50 U.S. servicewomen to advance sociological understandings of gender, femininity, and harassment. Recognizing that women are targeted with harassment throughout their military careers, I analyze specific episodes of harassment to examine organizational and interactional meanings and the power dynamics embedded in these instances. This article explains why servicemen escalate harassment toward women who are pregnant or who enter heterosexual relationships. In a militarized context that already denigrates femininity, I argue that men impose gendered and sexualized meanings on women’s life-course events to limit women’s organizational inclusion. These events, such as pregnancy and engagement or marriage to a heterosexual partner, serve as “femininity anchors” that tether women to femininity within a hyper-masculine environment. Femininity anchors present serious interactional and individual consequences for women as they attempt to navigate the gendered terrain of the U.S. military. Aside from eliciting moments of elevated sexual and nonsexual harassment, femininity anchors restrict women’s acceptance as real servicemembers and negatively affect their military careers. In highlighting the negative treatment women receive due to femininity anchors, I demonstrate how the specific ways gender is embedded in an organization shapes patterns of harassment and exclusion.