The aim of this study was to present our experience in the management of the recalcitrant upper lip and describe the surgical technique. We took a retrospective chart review of all patients who underwent reconstruction of the recalcitrant upper lip after maxillectomy and radiation therapy. Three female patients were identified. All patients had a history of malignant maxillary tumors, mucoepidermoid carcinoma (n = 1), verrucous carcinoma (n = 1), squamous cell carcinoma (n = 1). Tumor extirpation was carried out through total maxillectomy (n = 2), and bilateral subtotal maxillectomy (n = 1). Primary reconstruction was accomplished with scapula free flap (n = 1), fibula free flap (n = 1), and nonvascularized iliac crest bone graft (n = 1). Two patients underwent adjuvant radiotherapy. All patients developed recalcitrant upper lip. All patients had secondary reconstruction to correct of the recalcitrant upper lip using radial forearm free flap. All patients had successful dental rehabilitation. The mean follow-up was 5 years (range 3-7 years). Subjective functional and aesthetic outcome was assessed in all patients at the last follow up visit. All patients reported subjective improvement in speech, mastication and aesthetics. Free tissue transfer provides an ideal method to reconstruct the recalcitrant upper lip. Favorable functional and aesthetic outcomes can be successfully achieved using the technique described in this series.