This paper probes the disconnect between prison activists and the population they aim to defend. Activists in the California Coalition for Women Prisoners (CCWP), a women's prison organization which purports to represent female prisoners inside of three of California's women's penal institutions (Valley State Prison for Women, Central California Women's Facility at Chowchilla, and the California Institute for Women), are predominantly white, middle-class, highly educated and politically radical while the intended beneficiaries of their activism are predominantly of color, poor, and institutionally uneducated, in addition to being confined, silenced, and invisible from U.S. society at large. Acutely aware of the stark contrast between themselves and prisoners, as well as the privileges they enjoy from the very system they oppose, women in CCWP work to bridge themselves to their "sisters inside" while remaining conscious of the power differentials that separate them. Drawing on participant observation and interviews with both inmates and activists, I show that it is imperative for activists to see themselves, and to be seen by others, as representing the needs and interests of incarcerated women. In this frame, gender becomes the one pivotal property used to reconcile the dilemmas with which activists grapple. Yet, despite a broader radical agenda, activists end up affirming a conventional understanding of women's incarceration and abusive treatment by the legal system.