Objective It remains unclear whether postoperative complication rates and speech outcomes differ between patients undergoing primary versus secondary tracheoesophageal puncture (TEP) 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 a total laryngectomy (TL) or laryngopharyngectomy with pharyngeal free flap reconstruction for malignant disease. Data was collected on patient and operative demographics, postoperative complications, timing of TEP (primary or secondary), TEP speech outcomes, and predictive factors for TEP failure. Results Thirty patients (22%) had a primary TEP performed at the time of TL, 27 patients (20%) received secondary punctures (>3 months post TL), and 80 patients (58%) never received a TEP. Patient and operative demographics were similar between groups (p>0.05), apart from proportionately more hypopharyngeal tumors in the 'no TEP' group (p=0.002). Similar numbers of patients in primary and secondary TEP groups achieved functional speech (67% vs 71%, p=0.82). Median time to voice acquisition was 56 days for the primary group and 200 days for the secondary group. Salvage surgery and non-patch radial forearm free flap reconstruction both trended towards increased early postoperative complication rates (p=0.09).). Conclusion There is no difference in complication rates between primary and secondary tracheoesophageal puncture in patients undergoing total laryngectomy with concurrent free flap reconstruction. Radial forearm patch free flap reconstruction achieves good TEP speech outcomes.