Background: The aim of this study was to evaluate patient characteristics and findings after mammary ductoscopy in an effort to reduce the pain experienced during the procedure. Patients and Methods: We evaluated outpatients in whom mammary ductoscopy was performed under local or intraductal anesthesia without preference, and their clinical characteristics and findings were recorded. Average and maximum pain scores were determined after the examination for statistical analysis. Results: The overall average pain score was 3.74 ± 1.353, and the maximum pain score was 6.40 ± 1.681. The type of anesthesia, total operation time, nipple retraction, and discharge status significantly correlated with the pain score. Intraductal anesthesia lowered the average pain score by 0.60, whereas a total procedure time greater than 12 min increased the average pain score by 0.956. The pain score decreased if patients had nipple retraction, and intraductal anesthesia proved suitable for patients with normal nipples. Conclusion: Intraductal anesthesia is suitable for most patients, and ductoscopy should not exceed 12 min to minimize the pain. Nipple retraction does not significantly increase pain, but local anesthesia should be used in patients with retracted nipples. Patient age, breastfeeding history, menstrual stage, and presence of intraductal tumors were not associated with the level of pain experienced.