Purpose: Punctal stenosis can result in symptoms such as epiphora and can significantly reduce the quality of life of patients. Perforated punctal plug insertion is an easy procedure that is commonly used as the first step of treatment for punctal stenosis. Methods: Clinical, demographic, and outcome data were retrospectively collected for 54 eyes of 21 males and 11 females who consecutively presented to our Oculoplastic Clinic and underwent silicone Micro Flow perforated punctal plug insertion. All patients had epiphora with punctal stenosis. Results: Of the 54 plugs, 26 plugs (48.1%) were lost and 28 (51.8%) stayed in place. Of the latter, eight were explanted because of the occlusion of the plug with secretions and recurrent conjunctivitis; moreover, two plugs migrated deep into the vertical canaliculus. Of the 54 plugs, only 18 (33.3%) were well-tolerated with significant symptomatic improvement. Conclusion: Plug loss is a prominent problem in patients implanted with perforated punctal plugs. Silicone punctal plugs failed in 66.7% of our patients over a mean follow-up of 14.2 months.