Acquired reactive perforating collagenosis (ARPC) is a rare perforating dermatosis characterized by transepidermal elimination of altered collagen fibers. It is most commonly associated with diabetes and chronic kidney disease and may be underrecognized in patients with chronic pruritus. We report two cases of ARPC in women aged 74 and 60 years with type 2 diabetes who presented with severe chronic pruritus and multiple hyperkeratotic umbilicated papules. In the first patient, dermoscopy demonstrated crateriform lesions with a central keratotic plug, and histopathology revealed transepidermal elimination of degenerated collagen fibers. In the second patient, the diagnosis was suspected clinically and confirmed histologically using special stains. Clinicopathological correlation established the diagnosis in both cases. Treatment with systemic and topical therapies resulted in symptomatic improvement. ARPC is an uncommon and probably underdiagnosed dermatosis strongly associated with metabolic disorders, particularly diabetes and chronic kidney disease. These cases emphasize the importance of integrating clinical, dermoscopic, and histopathological findings to distinguish ARPC from other causes of chronic pruritus. ARPC should be considered in diabetic patients presenting with chronic pruritus and crateriform hyperkeratotic papules. Early recognition may facilitate timely diagnosis and optimization of associated systemic diseases.