Objectives: To determine whether postoperative complication rates and speech outcomes differ between patients undergoing primary versus secondary tracheoesophageal puncture following total laryngectomy with free flap reconstruction. Study Design: Retrospective clinical study in a tertiary academic center. Methods: Between November 2004 and June 2010, 137 patients underwent total laryngectomy or laryngopharyngectomy with pharyngeal free flap reconstruction for malignant disease. Data was collected on patient and operative demographics, early postoperative complications, speech outcomes, and predictive factors for tracheoesophageal puncture failure. Results: Thirty patients (22%) had a primary tracheoesophageal puncture performed at the time of laryngectomy, 27 patients (20%) received secondary punctures (>3 months postlaryngectomy), and 80 patients (58%) never received a puncture. Patient and operative demographics were similar between groups (P <.05), apart from proportionately more hypopharyngeal tumors in the "no puncture" group (P <.002). Similar numbers of patients in primary and secondary puncture groups achieved intelligible speech (67% vs. 71%, P =.82) and both groups reported good patient-perceived voice-related quality of life. Salvage surgery and nonpatch radial forearm free flap reconstruction both trended toward increased early postoperative complication rates (P =.09). Conclusions: There is no difference in the early postoperative complication rate for primary versus secondary tracheoesophageal puncture following total laryngectomy with concurrent free flap reconstruction. Radial forearm patch free flap reconstruction achieves good speech outcomes. Copyright © 2011 The American Laryngological, Rhinological, and Otological Society, Inc.