Purpose: Lacrimal drainage system probing and syringing is a commonly performed diagnostic procedure in the evaluation of tearing. However, we believe that the technique is not described in adequate detail in the medical literature. We describe our technique for reliable, safe, and pain-free assessment of the lacrimal drainage system. Case Report: A 65-year-old woman presented with bilateral intermittent tearing for 7 years. She demonstrated evidence of medial canthal tendon laxity, chronic anterior blepharitis, and significant elevation of the marginal tear film. An ophthalmology trainee, who was inexperienced in lacrimal drainage system syringing, assessed her. The patient sustained significant pain through the course of the procedure, which was therefore finally abandoned. No clinically useful information was obtained. Technique: A photographic analysis of our technique for lacrimal syringing is presented. It permits excellent lid stabilization by the dacryologist's left hand and total control of the barrel and cannula of the syringe by the dacryologist's right hand. A helpful feature is the use of an assistant to provide a third hand, which allows the dacryologist to evaluate the egress of fluid from the ipsilateral upper canaliculus during irrigation. Results: The described technique has been used successfully and with excellent results at the Ocular Plastics Unit of the Prince of Wales Hospital in Sydney, Australia, for more than 11 years. Conclusion: By following the steps described in the photographic analysis, lacrimal syringing can be performed in an atraumatic and systematic way that is beneficial for both patient and surgeon.