Objective: Endoscopic endonasal balloon-assisted dacryoplasty is a minimally-invasive surgical procedure that can be used in recurrent epiphora, a common pathology in both adulthood and childhood. Study design/Settings: We present a retrospective case series of eight patients who underwent trans-nasal balloon-assisted dacryoplasty after a failed external or endoscopic dacryocystorhinostomy, from March 2019 to January 2020, at the Department of Otolaryngology, San Raffaele Hospital, Milan, Italy. Subjects and Methods: All patients underwent routine preoperative work-up including fluorescein test (Jones test I–II), probing and irrigation of the lacrimal pathway and nasal endoscopy. Because of the recurrent nature of the pathology, pre-operatory computed tomography scan or dacryocystography was not performed. The surgical procedure was based on enlargement of the stenotic neorhinostomy created by primary dacryocystorhinostomy through the use of a high-pressure balloon catheter. Anatomical success was defined as a patent ostium on irrigation, whereas functional success was defined as free lacrimal flow on functional test and resolution of epiphora. Results: Anatomic and functional success was achieved in 100% of patients. Operative time ranged from 9 to 22 min (mean 16 min). No significant complications were reported. Conclusion: Our results indicate that trans-nasal balloon-assisted dacryoplasty can be considered as a safe and reliable surgical approach after a failed primary dacryocystorhinostomy. The shorter surgical time and reduced post-operative complication rates are the main advantages of this procedure.