Tracheoesophageal shunt insufficiency (TESI) is a common and potentially life-threatening complication after laryn(-gopharyn)gectomy (L(P)E). We investigated whether TESI could be the result of a specific shunt location. A monocentric, retrospective cohort analysis of 171 consecutively treated L(P)E patients was performed. Patients with a secondary prosthesis instillation and patients with insufficient postoperative imaging were excluded. Disease related data as well as location of primary voice prosthesis were assessed. The cohort was divided into 62 TESI-positive and 109 TESI-negative individuals. The mean time from surgery to TESI was 32 months. No differences were observed in gender, age, tumor localization, T/R/M-status. Surgery without adjuvant therapy was more often performed in TESI-negative individuals when compared with their positive counterparts. However, Cox regression including T/N status, therapy and categorized distance of the tracheoesophageal shunt to the manubrium (≤1.5 cm vs. >1.5 cm) revealed that a distance of ≤1.5 cm was associated with a 2.1-fold increased risk of TESI, while all other parameters did not influence the event-free survival. Primary shunt positioning ≤1.5 cm to the ridge of the manubrium is associated with an increased risk of TESI. In these individuals secondary shunt operation resulting in a position >1.5 cm distant to the manubrium should be recommended.