Aim: To assess various preoperative and peroperative clinical findings in endonasal dacryocystorhinostomy (DCR) as prognostic indicators of the surgical outcome. Materials and methods: A prospective study of 25 cases of chronic dacryocystitis with epiphora. All the patients were divided into two groups based on the presence or absence of medial canthal swelling with regurgitation of mucopus on finger pressure over medial canthus. Other factors included duration of epiphora, associated nasal problems, condition of the bone, sac wall, and lumen of the sac during surgery. Results: Out of 14 patients with medial canthal swelling (group I), all were successful on the table with free flow of saline, but one patient developed symptoms on 6 months follow-up and that was treated as failure. Out of 11 patients without medial canthal swelling, five were successful with free flow of saline on the table and six were unsuccessful because of tight or absent flow with regurgitation. Conclusion: Presence of medial canthal swelling and regurgitation of mucopus on digital pressure over medial canthus is a good prognostic indicator for a favorable surgical outcome. In patients without medial canthal swelling, we need to rely on syringing or dacryocystogram. Early intervention gives good results.