The aims of the current study were (1) to replicate findings regarding the mediator role of emotion regulation (ER) between attachment and empathy; (2) to extend current knowledge by testing the moderator effect of ER on the relationship between attachment and empathy; and (3) to test an integrative moderated mediation model in which attachment was hypothesized to moderate its indirect effect on empathy. The sample included 212 preschoolers aged three- to five-years old. Attachment, ER, and empathic perspective-taking were assessed by employing child interviews. The results confirmed that more secure attachment patterns foster higher ER awareness, which in turn is associated with higher levels of empathy; the strongest relationship between attachment and empathy occurs at below-average ER awareness; and the strength of the indirect effect of attachment on empathy through ER decreases as attachment security increases. These findings have implications for designing and implementing preventive interventions for preschoolers.