Purpose Lymphedema is a debilitating disease where the collected lymph fluid exceeds the lymphatic system’s ability to transport it, causing protein-rich fluid to leak into the tissues. Left untreated, this stagnant, protein-rich fluid can cause tissue to scar and interfere with wound healing which can result in lymphadenitis, and, in severe cases, skin ulcers, recurrent cellulitis, and death. In Australia, the main cause of lymphedema is due to cancer treatments. Many patients on breast cancer treatment would receive total axillary lymph node dissection (ALND) with about 20-40% developing upper limb lymphedema. Lymphovenous anastomosis (LVA) was described in the 1960s to bypass the accumulated fluid to the venous system. However, once the disease is established, despite LVA, it can still progress with inconsistent long term outcomes. Our study aims to apply the LVA technique concurrently with ALND to prophylactically prevent the incidence of lymphedema. Methodology We performed a prospective pilot study on 20 breast cancer patients undergoing total ALND with concurrent prophylactic LVA. Patient’s arms were measured pre- and post-surgery using circumference measurements at 5 different levels. Indocyanine green (ICG) mapping and L-Dex analysis were performed. Patients were followed up at 3, 6, 9 and 12 months. Results No patients have reported any symptoms of developing lymphedema. All patients showed stable circumference measurements, no dermal backflow on ICG, and a normal L-Dex range. Conclusion Our pilot study echoes with other international reports that prophylactic LVA reduces the incidence of lymphedema on patients undergoing ALND. Long term follow ups are required to substantiate this claim.