In 2014, following a notable influx of primarily Central American asylum-seekers arriving at the Mexico-U.S. border, two migrant detention centers were opened in small towns in South Texas. These facilities—known as the South Texas Family Residential Center and Karnes County Residential Center—functioned to detain a portion of these arrivals, mothers and their children, as they entered into legal proceedings. These so-called family detention centers, one of which is the largest migrant detention facility in the U.S., are visited daily by pro bono legal advocates who, among other things, assist the detainees with their asylum cases. My ethnographic research focuses on these advocates and their daily work at these facilities, asking: in what ways can we come to understand these increasingly unexceptional spaces through their unique ‘stranger’ perspective? My dissertation explores how these advocates, through their engagement with what I refer to as ‘legal care’, resist the myriad microlevel forms of punishment that mark administrative incarceration and asylum processes while simultaneously being implicated within such punitive regimes. My work considers the role of care not only in relations between detainees and advocates, but also in the grounded imbrications of humanitarian and administrative efforts. In aiding detainees, legal advocates are involved in the navigation of relationships with facility officials, such as guards, asylum officers, and immigration judges. My research points to the ways that care also marks and conditions these seemingly incidental relationships, weaving them within spatialized flows of care. Positioned from the perspective of these advocates, I argue that exploring the ‘ambivalent terrains’ and irrefutable tensions of care in and of this environment affords both a rich and uncomfortable encounter with the varied material and emotional entanglements involved in the incarceration of migrant families.