OBJECTIVE To report outcomes in free flap reconstructive surgery in the setting of calcified arteriosclerosis affecting the flap pedicle. DESIGN Retrospective review, including a detailed analysis of medical records, histopathologic findings, and a comprehensive review of the literature. METHODS A total of 1329 consecutive microvascular free tissue transfers were performed by 2 reconstructive surgeons at a university-affiliated tertiary care medical center from January 1, 1996, through December 31, 2011. Clinical notes, operative notes, and pathology reports were systematically reviewed to identify 44 patients (3%) with calcified arteriosclerosis involving the flap vascular pedicle. A comprehensive medical record review was performed for the included patients, detailing patient-related characteristics, flap survival, and incidence of perioperative complications. RESULTS A history of arteriosclerosis was identified preoperatively in 18 patients (41%). Eight patients (18%) were specifically recognized clinically and histologically to have a variant of arteriosclerosis known as Mönckeberg medial calcific sclerosis. In total, fibula osteocutaneous free flap was performed in 30 patients, radial forearm in 8 patients, rectus abdominus in 3 patients, latissimus dorsi in 2 patients, and parascapular in 1 patient. Perioperative complications occurred in 17 patients (39%), with the most common being pulmonary (14%) and cardiac (9%). Patient follow-up ranged from 3 to 137 months, with a mean postoperative follow-up of 21 months. The mean length of hospital stay was 12 days. There was a 0% incidence of total flap failure and a 7% incidence of partial flap necrosis. CONCLUSION Although technically challenging, successful microvascular free flap reconstruction can be achieved despite the presence of vascular calcifications affecting the flap vascular pedicle.