This study will be a double-blinded randomized controlled trial analyzing patients undergoing major lower extremity amputation by the vascular surgery service at UCSF Fresno between July 2017 and June 2018 at Community Regional Medical Center, Clovis Community Medical Center, and Fresno Heart and Surgical Hospital. All patients who have been evaluated by the vascular surgery service and have had lower extremity amputation deemed necessary based on ischemic disease, infectious disease, and/or disfiguration will be included. Patients will be excluded if they are less than 18 years of age, pregnant, undergoing emergency amputations, staged amputations, or amputations by non-vascular surgeons, have known allergies to bupivacaine, are unable to communicate symptoms of pain, or refuse to participate in the study. Eligible patients may be identified by the vascular surgery service in their private office or following a consultation by the vascular surgery service in the hospital. Upon identification, eligible patients or their surrogate decision maker will be approached for consent by a member of the study team.