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A 15-year-old healthy boy presented with multiple eruptive brown-colored to hyperpigmented papules all over the body for 1 year. His serum lipids were normal, and HIV serology was negative. Biopsy revealed hyperplastic epidermis along with an ill-defined lesion in the dermis that was composed of spindle-shaped fibroblastic cells and multiple cholesterol clefts within foamy macrophages. A diagnosis of cholesterotic dermatofibroma was made. The case is unusual for the young age of presentation and the presence of multiple eruptive papules.