<b><i>Purpose:</i></b> The aim of the study was to investigate the role of the exoscope as an assisting tool in endoscopic dacryocystorhinostomy (e-DCR). <b><i>Materials and Methods:</i></b> In this observational retrospective study, the application of the VITOM^® exoscope was studied in a group of 21 patients undergoing mono- or bilateral DCR. The primary endpoint was to evaluate resolution of symptoms (epiphora/dacryocystitis) at the 6-month follow-up and time for surgery. Qualitative features of the exoscope (intraoperative view of the surgical field) and comparison with the typical setting for DCR were analyzed as secondary endpoints. A questionnaire was administered to surgical team members (ENT surgeon, ophthalmologist, and scrub nurse) to evaluate the perceived quality of this new technology (12 items valued as “good” = 2, “acceptable” = 1, and “not acceptable” = 0). A questionnaire score of 24 out of 24 was valued as “completely approved,” score 20–23 as “moderately approved,” and score ≤19 as “weakly approved.” Patients were divided into 3 consecutive groups, and questionnaire scores by each team member were analyzed for tendencies. Statistical analysis was performed to test significance at <i>p</i> &#x3c; 0.05. Local Ethical Committee approval was obtained. <b><i>Results:</i></b> No significant differences were found between exoscope-set DCR and classic setting for concerned patient outcomes (failure rate: 3.2 vs. 3.8%, respectively, <i>p</i> = 0.896) and mean time for surgery (20’ vs. 23’, respectively, <i>p</i> = 0.091). The exoscope was valued by surgical team members as “completely approved” in 55.5% of cases, “moderately approved” in 39.7%, and “weakly approved” in 4.8%. Questionnaire scores by the ENT, ophthalmologist, and scrub nurse showed an average increase in the 3 consecutive groups (<i>p</i> = 0.119, <i>p</i> = 0.024, and <i>p</i> &#x3c; 0.001, respectively). <b><i>Conclusions:</i></b> The exoscope is a new tool that may support e-DCR. It has no effects on symptom outcomes (epiphora/dacryocystitis) and time for surgery compared to classic DCR. Based on self-perception, this new technology was accepted by all team members.