History reveals that the pathway toward carceral feminism was fraught with contradictions. Feminist reform strategies that appeared progressive devolved into mandates contributing to the policies of mass incarceration; frameworks meant to disavow racist myths of violence inherent to communities of color fueled color-blind narratives that cloaked white, middle-class-defined social movement priorities; safety strategies protecting survivors of violence entrapped them into set options violating the right to self-determination. Today's account of carceral feminism reveals well-intentioned choices leading to often ill-fated outcomes. As the critique of carceral feminism seeps into the discourse of the feminist anti-violence movement, a shift toward new values, policies, and practices holds the possibility of radical new directions. However, there is no reason to assume that this new pathway will be so straightforward. This article centers the dynamic of contradiction to synthesize insights of post-Marxist thought in application to contemporary anti-carceral feminist trends represented by transformative justice options. It also reflects on the recent ascendance of restorative justice and a renewed potential for carceral co-optation. The aim is to illuminate troubled areas of revision and radical alternatives and better navigate inevitable ethical and pragmatic tensions that may define future social movement trajectories.