An effort was made to develop a set of contextual models that would be appropriate to the study of families who undergo the family disruption of separation or divorce. The central idea is that contextual variables affect child adjustment only under conditions in which the social exchanges among family members are affected, particularly those associated with parenting practices. The data showed that the majority of the boys who developed antisocial problems after a separation tended to be in the early stages of school (K – 2). For these children, the hypothesis was the stressed/depressed mother would be most likely to have disrupted discipline practices with concomitant child adjustment problems. Several of the models showed that antisocial problems were related to a cascade of qualitatively new problems (e.g., school failure, rejection by normal peers, depressed mood). As those problems grew, they apparently contributed directly to future levels of maternal stress. Child deviancy, itself a product, seemed to function as a positive feedback loop that kept the process going. The second group of families at significant risk for increasing problems following separation were those in which the single mother repartnered within 4 years. Although this group showed reduced levels of stress, if they exhibited disrupted family problem-solving processes, their children were more likely to display increases in externalizing behaviors.