This chapter aims to critically examine the entanglements and contradictions between gender, feminism, penal policies, and prison practices in Portugal. Portuguese feminist literature has extensively explored questions around gender and prisons, centering on the context of women’s imprisonment. This body of work has highlighted the gender-specific challenges that shape the trajectories of incarcerated women, even though such insights have had little influence on penal policy. This chapter sheds light on a range of prison practices that fail to acknowledge the impact of gender expectations, roles, and relations on women inmates—despite improvements in the physical conditions of women’s prisons—and analyzes the formulation of penal norms and criminal justice procedures through a gender-sensitive lens (case 1). Also, although recent efforts have begun to incorporate LGBTQI+ perspectives into studies of gender and criminal justice, research on this topic remains limited in the Portuguese context. Accordingly, this chapter explores the challenges that LGBTQI+ individuals face within Portuguese prisons, which are largely ascribed to a lack of institutional preparedness and practical guidelines (case 2). The chapter concludes with a set of recommendations and future directions for research and policy development in this field.