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Imprisonment can severely impact and disrupt women’s childbearing and parenting experiences. Building on Sykes’ (1958) “pains of imprisonment” and the expanded “gendered pains of imprisonment” proposed by feminist scholars, this chapter examines the pregnancy and mothering experiences of 18 Filipino incarcerated women. This study has illuminated women’s diverse and distinct situations expressed in three broad themes: (a) lack of control and autonomy, (b) disrupted mothering role, and (c) social networks as coping resources. The findings demonstrated how women’s institutionally imposed “prisoner identity” overshadows their pregnancy status and mothering role, exacerbated by their experiences of systemic scarcity, restricted contact with family, and limited autonomy. Finally, the results illustrated how emotional and material support from social networks (family and prison peers) helped women cope with the pains of imprisonment.