Canaliculitis is defined as infection of the canalicular part of the lacrimal system. Despite usual presenting clinical characteristics such as pouting of the lacrimal punctum, discharge, and redness at the medial canthus area, it is usually misdiagnosed and overlooked. The presence of punctal ulceration and tissue necrosis is an uncommon presentation in these patients. We report a case of a 35-year-old female with a 3-day history of left lower eyelid medial swelling, tenderness, and discharge. She was found to have left lower eyelid diffuse conjunctival injection and swelling involving the lower lacrimal punctum with whitish necrotic tissue. The patient was taken to the minor treatment room and debridement of the necrotic tissue was done and swabs were taken for culture and sensitivity. The punctum was found to be open with deroofing of the proximal canalicular system due to the severe nature of the infection; this was followed by irrigation using moxifloxacin and povidone-iodine. The patient was started on systemic antibiotics, topical antibiotic eye drops, and povidone-iodine sticks to clean the affected area. Few days later, the microbiology results revealed infection by Pseudomonas aeruginosa, and the patient was improving gradually until she had complete resolution of the infection.