Topical corticosteroids are first-line treatment for many dermatoses, and are generally considered safe and effective. However, topical steroid withdrawal syndrome can result from use of topical corticosteroids, and this condition is not well-known among physicians. This article reports a mother and son whose presentations of topical steroid withdrawal syndrome following the discontinuation of prolonged, high-potency topical corticosteroid use were nearly identical. This report adds to the growing body of evidence that topical steroid withdrawal syndrome is its own entity, rather than an exacerbation of the underlying dermatosis, and adds to the few pediatric reports of topical steroid withdrawal syndrome. Management for both patients involved topical corticosteroid discontinuation; however, it took approximately 2 years before the majority of their topical steroid withdrawal syndrome manifestations resolved. Increased awareness surrounding this condition is essential to facilitate topical steroid withdrawal syndrome prevention and diagnosis and to decrease topical corticosteroid phobia and increase patient-physician trust.