This article argues that Orange Is the New Black (OITNB) uses postfeminist strategies to covertly promote prison reform and exercise a subtle critique of (female) mass incarceration while remaining constrained by the limitations of a postfeminist sensibility. Despite its contradictory and uneven agenda, OITNB should be seen as an important ally in the process of raising awareness about media (mis)representations of female prisoners, not least because of the program’s own self-reflexive commentary on tropes of the women in prison genre. The article calls for a tactical alliance between academic examinations of female imprisonment and critical sensibilities in popular culture to further more fundamental critiques of women’s incarceration, and its concomitant cost to individuals, families, and society.