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Punctal occlusion is a common therapy for dry eye syndrome using permanent or biodegradable plugs to reduce tear drainage. This case describes a female in her 60s who developed left inferior canaliculitis 4 days after receiving biodegradable plugs. Surgical exploration removed one biodegradable plug and five retained silicone plugs, previously assumed to have extruded. Given that silicone plugs are a well-established risk factor for canaliculitis, the presence of multiple retained silicone plugs likely represents a significant predisposing factor. Although the acute timing of symptoms following biodegradable plug insertion suggests it may have served as a precipitating factor, causality cannot be established; its role should be interpreted within the context of the existing foreign material. The infection resolved with surgery and antibiotics. This case highlights the importance of confirming canalicular patency before inserting new plugs, as reliance on visual absence alone may overlook retained plugs and increase the risk of complications.