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The anticipatory stress stemming from criminal justice contact is one potential explanation for the deleterious consequences of incarceration for the health of confined individuals and their family members, but little research considers these processes. In this paper, we use data from the Jail & Family Life study, a longitudinal interview study of men incarcerated in Southern California and their family members to explore processes of anticipatory stress that stem from jail incarceration. Data from 335 in-depth interviews suggest three primary conclusions. First, anticipatory stress during jail incarceration is pervasive among both fathers and their family members. Second, anticipatory stress commonly centered around one of three domains: (1) anticipatory stress surrounding the adjudication of one’s case; (2) anticipatory stress about reintegration back to families and communities after release; and (3) anticipatory stress regarding the maintenance of family relationships and the wellbeing of loved ones. Across all domains, anticipatory stress necessitates major changes, involves considerable unpredictability, and facilitates feelings of powerlessness. Third, though families adopt strategies to cope with the incarceration by turning to religion and by actively searching for distractions, the uncertainty associated with incarceration leaves considerable uncertainty about future plans and hinders families’ ability to make important life decisions.