Rationale: This case report highlights the complexities involved in diagnosing and managing a lesion in the medial canthal region, particularly when complicated by dacryocystitis and nasolacrimal duct obstruction (NLDO). The case underscores the importance of a multidisciplinary approach and surgical intervention in restoring lacrimal function and improving patient quality of life. Patient Concerns: A 27 year-old female presented with a persistent ulcerative lesion on the medial aspect of her left upper eyelid, associated with dacryocystitis and epiphora. The patient had a history of similar symptoms and underwent prior surgical excision and cataract surgery, which did not resolve her condition. Diagnosis: Clinical examination revealed a pustulous lesion adjacent to the medial canthus, with imaging studies (CT and USG) suggesting a neoplastic or granulomatous etiology. A final diagnosis of a neoplastic/granulomatous lesion was made, complicating dacryocystitis. Interventions: The patient underwent surgical excision of the lesion, dacryocystorhinostomy (DCR), and medial canthoplasty using a palmaris longus tendon graft. The surgery aimed to address both the structural and infectious components of the pathology. Outcomes: The surgical intervention successfully restored the lacrimal system function, alleviated symptoms, and achieved satisfactory cosmetic results. A three-week follow-up showed good healing and resolution of the patient's complaints. Lessons: This case emphasizes the need for a comprehensive diagnostic approach, combining clinical evaluation with advanced imaging. It also highlights the critical role of surgical procedures like DCR and medial canthoplasty in managing complex lacrimal and periocular conditions, ensuring favorable patient outcomes.