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The reactivity-regulation model suggests that the origins and maintenance of shyness results from relatively high levels of reactivity in combination with relatively low levels of regulation. Although this model has received limited empirical support, there are still many issues regarding directionality of the relations among shyness, reactivity, and regulation, as well as a dearth of studies examining the joint influence of reactivity and regulation on the prospective development of shyness as suggested by the model. Using a short-term prospective longitudinal, cross-lagged design, we first examined whether the relations among reactivity, regulation, and shyness were unidirectional or bidirectional in a sample of 1313 children (49.8% female) assessed annually across three waves from middle childhood (Mage = 10.72) to early adolescence (Mage = 12.42)., We then performed a latent growth curve analysis to examine whether reactivity and regulation interacted to influence the development of shyness over time. We found that the relation between reactivity and regulation and shyness were unidirectional. At Wave 1, shyness was related to higher levels of reactivity and lower levels of regulation at Wave 2, but neither reactivity nor regulation at Wave 1 predicted shyness at Wave 2. At Wave 2, shyness predicted greater reactivity at Wave 3, but shyness at Wave 3 was only predicted by lower levels of regulation at Wave 2. Contrary to the reactivity-regulation model of shyness, we also found that relatively high levels of reactivity and low levels of regulation predicted a steep decrease in shyness over 3 years, whereas relatively high levels of reactivity and high levels of regulation predicted more stability in shyness over time. These results are discussed in the context of the socioemotional difficulties sometimes experienced by shy individuals and demonstrate the importance of empirically evaluating long-standing models of personality development.