Chylous leakage is a rare surgical complication most frequently encountered following operations involving the neck and thorax. Even more rare are axillary chyle leaks secondary to breast cancer involving the axillary lymph nodes. Anatomic variability in the termination of the thoracic duct may play a role in the susceptibility some individuals may have to this type of leakage. There is no consensus on the definitive management of these complications, especially in the context of breast reconstruction. Here, we report our experience in the management of chylous leakage in three patients who underwent left axillary lymph node dissection and immediate breast reconstruction with the use of tissue expanders and acellular dermal matrix. Descriptions of each case are followed by a review of the relevant literature. We also present an original treatment algorithm. Two of three patients with suspected chylous leakage secondary to intraoperative injury to the axillary region underwent definitive diagnosis by clinical examination and drain fluid triglyceride analysis, followed by conservative management with a low-fat diet. The third patient was diagnosed clinically with no fluid analysis. All leakages resolved through conservative means, with no need to return to the operating room for surgical exploration and repair. Based on our experience, we believe that patients with suspected chylous leakage secondary to axillary lymph node dissection in the context of breast reconstruction can be safely and effectively managed by conservative management in the acute postoperative period. If these measures are insufficient, surgical management may be necessary.