Purpose: To evaluate the improvement in epiphora and need for surgical revision in patients with acquired nasolacrimal duct obstruction following balloon-assisted, middle meatal endoscopic dacryocystorhinostomy with chitosan-based dressing versus bioresorbable polyurethane packing versus no packing. Patients and Methods: This was a retrospective study of consecutive adult patients seen from 2015 to 2018 with follow-up evaluation of epiphora at least 3 months after balloon-assisted, middle meatal endoscopic dacryocystorhinostomy. Patients with a history of prior punctoplasty, septoplasty, sinus surgery, or dacryocystorhinostomy of any kind were excluded. Those meeting criteria were stratified by postoperative hemostatic intervention: no packing, bioresorbable packing, and chitosan-based dressing (groups 1, 2, and 3, respectively). Procedural outcomes were graded as successes or failures based on subjective report and anatomical findings at most recent visit within an 18-month postoperative window. Instances of recommendation for revision surgery were also recorded. Results: Forty-three cases (36 patients) met the abovementioned criteria. Groups 1, 2, and 3 comprised 12, 17, and 14 cases each, respectively. Average patient age was 55.3 years old, and average duration of follow-up was 6.7 months. Significant variation in outcomes was detected across the 3 groups ( P = .0495), particularly between groups 1 and 3 ( P = .033). Use of chitosan-based dressing trended toward reduced rates of recommendation for surgical revision ( P = .203, P = .113). Conclusions: Use of chitosan-based dressing after endoscopic dacryocystorhinostomy was associated with improved subjective and anatomical outcomes. It may also contribute to less frequent need for revision surgery. Further study in a larger prospective trial is recommended.