Papulosquamous disorders constitute one of the common pediatric dermatoses. They are a heterogeneous group consisting of psoriasis, eczema, pityriasis rubra pilaris, and other conditions, where the differential diagnoses are close to each other clinically. Moreover, the presentation of the same disease in children can differ from that occurring in adults. We report two infants with erythematous scaly papules and plaques diagnosed as two different disorders, albeit with a grossly similar appearance. Both these dermatoses are considered to be quite uncommon in infancy and can pose significant challenges in management. These disorders sometimes present with atypical variants, rendering it increasingly difficult to distinguish them. Some of these disorders tend to progress to erythroderma, and the infant may occasionally present directly in the erythrodermic stage, further compounding the conundrum. In such situations, identification of subtle clinical and histopathological clues allows accurate diagnosis, which is imperative for appropriate prognostication and treatment. This article illustrates the importance of histopathology and immunohistochemistry in aiding diagnosis and outlines the management of these disorders while emphasizing the importance of timely intervention in averting inadvertent complications in these young individuals.