Background: Postoperative pain and analgesic use after arthroscopic rotator cuff repair remain important issues that affect rehabilitation and overall outcomes. Purpose: To evaluate the pre- and intraoperative factors that may cause prolonged duration of postoperative pain and analgesic use. Study Design: Case-control study; Level of evidence, 3. Methods: We included 443 patients who underwent arthroscopic rotator cuff repair and subacromial decompression. Visual analog scale (VAS) scores for pain were obtained preoperatively and at 30 and 90 days postoperatively. Patients were divided into a group who had prolonged postoperative pain (duration >= 1 and <3 months; n = 86 patients) and a group with nonprolonged pain (duration <1 month; n = 357 patients). The following factors were compared between groups: age, sex, body mass index, repair technique, tear size, retraction amount, repair tension, tendon degeneration, preoperative pseudoparesis, symptom duration, application of microfracture to the rotator cuff footprint for marrow stimulation, smoking, degree of fatty degeneration, preoperative narcotic analgesic use, diabetes, acromioclavicular joint degeneration, and preoperative Douleur Neuropathique 4 (DN4) and American Shoulder and Elbow Society (ASES) scores. Results: Significant differences were seen between the prolonged and nonprolonged groups regarding the median duration of pain (54 vs 27 days, respectively; P < .001) and analgesic use (42 vs 28 days, respectively; P < .001). Significant differences were noted between the groups for symptom duration (P = .007), smoking status (P = .001), degree of fatty degeneration (P = .009), preoperative narcotic analgesic use (P < .001), preoperative DN4 and ASES scores, 30-day VAS score (P < .001), duration of opioid and nonopioid analgesic use (P < .001), tear size (P = .026), and retraction stage (P = .032). Tear size (P = .009), retraction amount (P = .005), preoperative narcotic analgesic use (P < .001), degree of fatty degeneration (P < .001), and preoperative DN4 score (P = .024) were factors independently associated with prolonged postoperative pain and analgesic use. Conclusion: Patients with larger size tears, retracted tendons, preoperative use of narcotic analgesics, higher tensioned tendon after repair, and Goutallier grade 3 or 4 fatty degeneration faced an increased risk of prolonged postoperative pain and analgesic use after arthroscopic rotator cuff repair. These factors might be mitigated by psychosocial support; gentle, controlled, and individualized postoperative rehabilitation approaches; detailed preoperative evaluation; and closer follow-up of patients who are treated operatively.