Aesthetic outcomes are key determinants of psychosocial functioning among surgically treated patients with head and neck cancer (HNC); however, long-term aesthetic outcomes after microvascular free tissue transfer (MFTT) are not well described. To examine risk factors for impaired long-term aesthetic satisfaction and appearance-related psychosocial functioning after HNC ablation with MFTT. A cross-sectional, web-based survey was conducted at an academic tertiary care center. A total of 228 individuals who underwent MFTT between January 1, 2015, and December 31, 2019, for treatment of HNC were included. The study was conducted from November 1, 2020, through January 15, 2021. Head and neck cancer ablation with MFTT. Patient-reported outcomes were assessed via Aesthetic FACE-Q scales. The primary objective was aesthetic satisfaction determined by the Satisfaction With Facial Appearance scale. Secondarily, the Appearance-Related Psychosocial Distress, Psychological Function, and Social Function scales were used to assess appearance-related psychosocial functioning. Patients were stratified by demographic, disease, surgical, and postoperative characteristics. Survey scores on a 100-point scale were compared and subjected to univariable and multivariable linear regression. A total of 124 of 228 patients (54.4%) completed surveys a median of 34.4 months after MFTT (interquartile range, 22.6-48.8). Most responders (79 [63.7%]) were men with advanced cancer of the oral cavity or skin, reconstructed with anterolateral thigh or osteocutaneous fibula free flaps. Nonresponders had no significant differences in baseline characteristics. The Satisfaction With Facial Appearance score was independently lower among patients who received osteocutaneous flaps (regression coefficient, -10.6 points, 95% CI, -20.4 to -0.8 points) and/or adjuvant (chemo)radiotherapy (regression coefficient, -6.9 points; 95% CI, -13.8 to -0.1 points). Impaired appearance-related psychosocial functioning was independently associated with female sex, a history of anxiety or depression, osteocutaneous flaps, prolonged tube feeding requirements, and any recurrent or persistent disease. After adjustment for covariates, each 1-point increase in the Satisfaction With Facial Appearance score independently estimated improved appearance-related psychosocial functioning as determined by the Appearance-Related Psychosocial Distress scale (regression coefficient, -0.5 points; 95% CI, -0.7 to -0.4 points), Psychological Function scale (regression coefficient, 0.4 points; 95% CI, 0.3 to 0.5 points), and Social Function scale (regression coefficient, 0.4 points; 95% CI, 0.3 to 0.6 points). The findings of this cross-sectional, web-based survey study suggest that osteocutaneous reconstruction and adjuvant therapy independently increase the risk of poor patient-reported long-term aesthetic satisfaction, which correlated with impaired appearance-related psychosocial functioning. Aesthetic outcomes appear to be a priority to address in patients with HNC undergoing MFTT.