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Diffuse dermal angiomatosis (DDA) is a rare, benign cutaneous disorder that can affect the breasts. Typically, it presents in middle-aged women and is increasingly associated with various risk factors that involve tissue hypoxia. We report this case of classical bilateral DDA of the breasts in a 56-year-old female patient. This case highlights the association of DDA with hypoxia-inducing risk factors, such as smoking. Management of the hypoxic risk factors resulted in the resolution of the bilateral ulceration caused by DDA in this patient. This case report aims to discuss the etiology, risk factors, clinical manifestations, and treatment modalities commonly used to manage this condition., Competing Interests: Human subjects: Consent was obtained or waived by all participants in this study. Conflicts of interest: In compliance with the ICMJE uniform disclosure form, all authors declare the following: Payment/services info: All authors have declared that no financial support was received from any organization for the submitted work. Financial relationships: All authors have declared that they have no financial relationships at present or within the previous three years with any organizations that might have an interest in the submitted work. Other relationships: All authors have declared that there are no other relationships or activities that could appear to have influenced the submitted work., (Copyright © 2024, Shet et al.)