A prospective study examined the effects of maternal unresponsivity and of toddlers' own negative affect on the child's subsequent ability to use effective attentional control strategies in preschool. Maternal and child behaviors were measured in situations that varied in the level of stress to test the hypothesis that behaviors in high stress situations would be more diagnostic of children's subsequent self-regulatory behavior. As predicted, both maternal unresponsivity and toddlers' negative affect, particularly in a high stress as opposed to a low stress situation, predicted children's later use of ineffective attentional control strategies. Similarly, maternal disengagement that occurred contingent to toddlers' distress predicted ineffective attentional control strategies whereas maternal disengagement in response to toddlers' non-distress behaviors did not. The findings supported the utility of a contextual approach to understanding the impact of maternal and child characteristics on the development of self-regulatory skills.