A retrospective longitudinal cohort study included 561 women after surgical evacuation of a missed abortion who were divided into three groups: no estrogen, with oral estrogen, and with transdermal estrogen. Endometrial thickness at 1 and 3 months was significantly greater in both estrogen groups compared to the no estrogen group (p < 0.001 and p = 0.001), with the transdermal group showing the best results. Decreased menstrual flow was less frequent in estrogen-treated women (p = 0.022). Oral estrogen was associated with more frequent breast tenderness and systemic symptoms, whereas transdermal estrogen had better adherence (68.3% vs. 46.7%, p < 0.001). After 1 year of follow-up, pregnancy outcomes were not significantly different between groups (p = 0.819), although a higher conception rate was observed in the estrogen groups, especially with transdermal therapy. The study confirms that postoperative estrogen therapy promotes endometrial recovery and may improve reproductive prognosis, while transdermal estrogen is better tolerated. Further prospective studies are needed to confirm these findings.