Samia Sultana Anny, a 40-year-old housewife, presented with watering and purulent discharge from her left eye for 4 years and 1 year, respectively. Examination revealed matted eyelashes, full lacus lacrimalis, and a positive regurgitation test on the left side, indicating chronic dacryocystitis. Investigations and management with left dacryocystorhinostomy and intubation were planned. Differential diagnoses included acute dacryocystitis and punctum stenosis.