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Abstract: Insulin-derived amyloidosis (AIns) is a rare iatrogenic subtype of cutaneous amyloidosis occurring at frequent insulin injection sites. Here, we describe 2 cases of AIns accompanied by acanthosis nigricans (AN)-like changes, a rare finding which has been reported fewer than 5 times in the literature. We also report the first case of an AIns nodule being misdiagnosed as a keloid. Both of our patients presented with asymptomatic, hyperkeratotic, pigmented plaques at frequent insulin injection sites, and histopathologic examination showed (1) nodular aggregates of amyloid demonstrating apple-green birefringence with Congo red staining and (2) AN-like features, such as epidermal papillomatosis, hyperkeratosis, and hyperpigmentation. Accurate diagnosis of AIns is crucial, because repeated insulin injection into a nodule can impair glycemic control. However, misdiagnosis is common, as observed with our second patient, whose AIns nodule was misdiagnosed by an outside provider as a keloid, perhaps because of the presence of AN-like features. Our case report adds to the limited but growing body of literature on AIns and significantly increases the number of reported cases of AIns with AN-like features, an even rarer phenomenon., Competing Interests: The authors declare no conflicts of interest. Dr. Rosalie Elenitsas has no conflicts of interest relevant to this manuscript. However, for full disclosure: she has received royalties from Wolters Kluwer as a textbook editor., (Copyright © 2022 Wolters Kluwer Health, Inc. All rights reserved.)