Deportees, more than other potential migrants, are particularly likely to have strong family connections to the United States. It is important to study deportee decision-making because of the unique nature of deportees’ connections to the U.S. and to family members living there. While it is known that familial connections play a large role in deportee migration motivation, the complexity of this motivation remains underexplored. Why do some deportees with family in the U.S. attempt to cross the border, while others do not? How does the nature of the familial bond affect the decision to migrate? How does deportees’ experience with the American carceral system affect their dedication to family, and thus their motivation to migrate? My qualitative examination of deportee interview transcripts shows that, for many, the desire to reunite with family is often prioritized over other practical considerations. My main argument is that deportees who have outwardly similar cross-border family connections are inclined towards different migration decisions depending on their level of emotional attachment towards family members in the U.S. Affectual connection to family appears to take precedence over issues of stigma or status, and over notions of national affiliation with the U.S. or Mexico. In some cases, emotional connections can be severely strained and degraded by the aspects of the deportation process, especially lengthy incarcerations. Not only is this breakdown of family ties extremely painful for the parents, children, and other family members; it likely also has a corrosive effect on overall societal stability.