Triple-negative breast cancer (TNBC) refers to a heterogeneous group of carcinomas that have more aggressive biologic features, faster growth, and a propensity for early distant metastasis and recurrence compared with other breast cancer subtypes. Due to the aggressiveness and rapid growth of TNBCs, there are specific imaging challenges associated with their timely and accurate diagnosis. TNBCs commonly manifest initially as circumscribed masses and therefore lack the typical features of a primary breast malignancy, such as irregular shape, spiculated margins, and desmoplastic reaction. Given the potential for misinterpretation, review of the multimodality imaging appearances of TNBCs is important for guiding the radiologist in distinguishing TNBCs from benign conditions. Rather than manifesting as a screening-detected cancer, TNBC typically appears clinically as a palpable area of concern that most commonly corresponds to a discrete mass at mammography, US, and MRI. The combination of circumscribed margins and hypoechoic to anechoic echogenicity may lead to TNBC being misinterpreted as a benign fibroadenoma or cyst. Therefore, careful mammographic and sonographic evaluation with US image optimization can help avoid misinterpretation. Radiologists should recognize the characteristics of TNBCs that can mimic benign entities, as well as the subtle features of TNBCs that should raise concern for malignancy and aid in timely and accurate diagnosis. ©RSNA, 2023 Quiz questions for this article are available in the supplemental material.