Background: Fulfillment of patients’ expectations following foot and ankle surgery has been previously studied, and shown to be an effective modality in assessing patient-reported outcomes (PROs). Although this assessment has been shown to correlate well with patient satisfaction and other validated PROs, the impact of postoperative complications on fulfillment of expectations is unknown. The aim of this study is to therefore investigate the impact of postoperative complications on fulfillment of patients’ expectations. Methods: Preoperatively, patients completed a validated Foot and Ankle Expectations Survey consisting of 23 questions encompassing domains including pain, ambulation, daily function, exercise, and shoe wear. At 2 years postoperatively, patients answered how much improvement they received for each item cited preoperatively. A fulfillment proportion (FP) was calculated as the amount of improvement received versus the amount of improvement expected. Chart review was performed to identify patient demographics, comorbidities, pain management, and postoperative complications, which were classified as minor (infection requiring antibiotics) or major (return to operating room for revision, deep infection). FP in patients with a complication was compared to patients who did not experience a complication. In addition, the Foot and Ankle Outcomes Score (FAOS), satisfaction, and Delighted-Terrible scale (how they would feel if asked to spend the rest of their life with their current foot/ankle symptom) were collected at final follow-up. Of the 271 patients (mean age 55.4 years, 65% female), 31 (11.4%, mean age 53.6, 58% female) had a postoperative complication: 25 major (19 revisions, 6 deep infections requiring irrigation and debridement), 4 minor (4 superficial infections requiring antibiotics), and 2 major and minor (revision and superficial infection). Average time from complication to completion of fulfillment survey was 15 (±3.6) months. The groups were similar in diagnoses. Results: Complications were associated with significantly worse FP (0.69 ± 0.45 vs 0.86 ± 0.40, P = .02). Having a complication significantly correlated with worse satisfaction, Delighted-Terrible scale, and FP ( P < .001). FAOS domains were similar between groups preoperatively; postoperatively, patients without complications had significantly higher Activities of Daily Living and Quality of Life scores ( P < .05). Demographically, there was no difference in age, sex, body mass index, Charlson Comorbidity Index, depression/anxiety, or pain management between the 2 groups. Conclusion: Our data suggests that postoperative complications following foot and ankle surgery were associated with worse patient-reported fulfillment of their operative expectations even after recovery from the initial surgery and complication. This finding is independent of preoperative expectations, and correlates with patient satisfaction with their procedure. Therefore, while patient-perceived fulfillment following foot and ankle surgery is multifactorial, the incidence of a postoperative complication negatively impacts fulfillment as well as satisfaction following surgery. Level of Evidence: Level II, prospective comparative series.