Objective: To discuss the removal time of a nasolacrimal silicone tube stent by reporting three cases with canalicular laceration due to prolonged indwelling of the stent. Methods: This study involved three cases of nasolacrimal duct obstruction treated by endoscopic dacryocystorhinostomy with silicone tube insertion. Results: The mean indwelling time of the silicone tube was 9.3 months and all of the patients had lower canalicular laceration near the common canaliculus. One patient presented with a complaint of canthal pain, blurred vision, and epiphora while the other two patients reported no complaint. The nasal endoscopic examination revealed a narrow fibrotic ostium below the medial concha. The silicone tubes were removed. Conclusions: To increase the success rate of the operation, the removal time for nasolacrimal silicone tubes after dacryocystorhinostomy is also important. Our findings indicate that physicians should be aware of the potential problems related to prolonged intubation.