Self-regulation is the ability of a child to control emotion, cognition, and social behavior. This study examined self-distraction as a form of self-regulation. Eighty-five 4-year-olds and their mothers participated in this study. The purpose of the study was to explore preschoolers self-distraction, including attentional and behavioral, in two waiting contexts (mother absent vs. mother present). This study also explored the association of different maternal regulation strategies with preschoolers self-distraction and investigated individual child characteristics such as sex, age, temperament, and language ability in relation to preschoolers use of self-distraction. Results revealed that male and female preschoolers differed in the duration of their use of regulatory strategies. Preschoolers use of self-distraction was context-dependent; they performed attentional distraction more frequently, longer, and quicker in their mothers absence and performed behavioral distraction more frequently, longer, and quicker in their mothers presence. Maternal insufficient regulation and ignore was the strongest predictor of reduced duration of child attentional distraction. Childrens characteristics, in general, were not related to their use of self-distraction. Implications and directions for future studies are discussed.