Breast cancer is the most common malignancy diagnosed during pregnancy. Breast cancer during pregnancy or within the first postpartum year is commonly described as Pregnancy-Associated Breast Cancer (PABC). PABC often exhibits poorer histopathologic features and has a worse prognosis when compared to young breast cancer patients without a current or recent pregnancy. Here, we describe two cases of PABC in which the presenting symptoms of the patients were interpreted as pregnancy-related changes, causing a diagnostic delay. Therefore, we argue that every pregnant or postpartum woman with changes in the breast must be thoroughly evaluated to exclude the possibility of a malignancy. In case of any suspicion, patients must be referred to a breast cancer center for further evaluation.