Shared residence after divorce is rising in most Western countries and legally recommended by law in Belgium since 2006. Living with both parents after divorce is assumed to increase children's well-being, through a better parent-child relationship, but may also be stressful, as children live in 2 different family settings. In this study, we investigate whether the association between the residential arrangement of adolescents and 3 measures of subjective well-being (depressive feelings, life satisfaction, and self-esteem) is moderated by the Big Five personality factors. The sample is selected from the national representative Divorce in Flanders study and contains information about 506 children from divorced parents between 14- and 21-years-old. Our findings indicated a consistent pattern of interactions between conscientiousness and joint physical custody for 2 of the 3 subjective well-being indicators. The specific demands of this residential arrangement (making frequent transitions, living at 2 places, adjustment to 2 different lifestyles, etc.) may interfere with the nature of conscientious adolescents: being organized, ordered, and planful. Our results showed support for a Person × Environment interaction, and demonstrate the need for considering the individual characteristics of the child when settling postdivorce residential arrangements.