The purpose of this article was to specify the relation between parenting stress and the early behavioral organization of 2-year-olds. Twenty-seven families provided assessments of parental stress and child behavior problems. In addition, observations of toddler pretend play and autonomy development were conducted. Mothers who reported higher levels of stress within areas of life related to parental adjustment (e.g., relationship with spouse, social isolation, health) had toddlers who exhibited more externalizing and total behavior problems. In addition, mothers who reported higher levels of stress in relation to their toddler (e.g., perceptions of reinforcement from child) were more likely to have toddlers who exhibited behavior problems, less pretend play, and less usage of self-assertion during home observations. Finally, fathers who reported higher levels of stress in relation to their toddler also reported more behavioral problems.