Regulatory flexibility is the ability to meet demands of a situation by modulating behavior, cognitions, or emotions. While flexibility has been studied in early childhood, the role of reactive and regulatory temperamental building blocks of flexibility to meet requirements of different contexts has not been investigated in preschoolers. Routine and novel contexts require very different skills to navigate appropriately. For example, different aspects of inhibition and modulation of behavior may come into play in familiar/routine and novel contexts such those that depart from expectations. The current study utilized a parent-report measure of temperament and of regulatory flexibility to address the unique contributions of selected temperamental attributes—including attention, sensitivity, and activity level—to regulatory flexibility. Because of its multi-faceted nature (Kashdan & Rottenberg, 2010), an in-depth examination of regulatory flexibility could provide a better understanding of how preschoolers meet the challenges that are introduced to them during this developmental period.