Purpose Endoscopic endonasal balloon-assisted dacryoplasty is a minimally invasive surgical approach that can be applied after failure of dacryocystorhinostomy with recurrence of distal acquired lacrimal obstruction. Methods At the Department of Otolaryngology, San Raffaele Hospital, Milan (Italy), from December 2016 to October 2020, 14 patients underwent trans-nasal balloon-assisted dacryoplasty after a failed dacryocystorhinostomy (both external and endoscopic endonasal). The routinary pre-operative work-up included multidisciplinary study of the lacrimal disease, which consisted in primary ophthalmological and otorhinolaryngological visits associated with nasal endoscopy, in which a radiological exam was added if needed. The surgical approach includes pneumatic enlargement of the stenotic rhinostomy, created during the primary dacryocystorhinostomy, using a high-pressure trans-nasal balloon catheter. Anatomical success was considered when the ostium was patent upon irrigation, while functional success was considered as resolution of epiphora or free lacrimal flow on functional test. Results Among 14 patients included and after a mean follow-up of 19.5 months (range 13-51 months), anatomic success was achieved in 100% of patients and functional success was achieved in the 85.7% (12/14). Operative time ranged from 9 to 28 min (mean 18 min) and no complications were reported. Conclusion Trans-nasal balloon-assisted dacryoplasty is a mini-invasive surgical approach to treat failed dacryocystorhinostomies with reliable and stable outcomes in the long term. The absence of post-surgical complications, high success rate and short operative time are the main features of this innovative procedure.