A device for inserting a flexible silicone intubation stent into the lacrimal drainage system of a patient. The device has an oblong hollow semi-rigid probe having the flexible stent releasably secured to its blunted distal end. The probe and stent are oriented in a side-by-side configuration for endwise insertion into the punctum. The stent can be temporarily secured to the distal end of the probe by engaging the probes distal opening. The stent can be detached by injecting a pressurized fluid through the channel of the probe thereby forcing the distal end of the stent to pop off. The proximal extremity of the stent is secured in the patient by an integrated or separate punctal anchor.