Emotion regulation includes the ability to up-regulate or enhance the emotional reaction and downregulate or suppress the emotional reaction in accordance with situational demands. However, children's use of enhancement strategies has been neglected, as has the examination of whether they can flexibly alternate between enhancement and suppression strategies. In the present study, we examine whether preschool children (N = 61) can intentionally enhance and suppress their emotional expression based on situational demands and its association with modulating their expression in a real-world situation requiring emotion regulation demands. Our findings provide initial evidence that three-year-old children can enhance positive and negative emotional expressions when the situation demanded, with the former being associated with more adaptive emotion regulation strategies in a social situation. The current study identifies expressive emotion enhancement as an emergent skill during the preschool period that may have broader implications for children's socio-emotional functioning.