To identify technologies associated with the least operative pain in women undergoing operative office hysteroscopic procedures. Data Sources: MEDLINE, Embase, Cumulative Index to Nursing and Allied Health Literature, and Cochrane Central Register of Controlled Trials were searched until January 2021 using a combination of keywords "hysteroscop*," "endometrial ablation," "outpatient," "ambulatory," "office," and associated Medical Subject Headings. Methods of Study Selection: Randomized controlled trials evaluating the effect of hysteroscopic devices on pain experienced by women undergoing operative office hysteroscopy were included. Data were also collected regarding efficacy, procedural time, adverse events, and patient/clinician acceptability and/or satisfaction. Tabulation, Integration, and Results: The search returned 5347 records. Ten studies provided data for review. Two trials compared endometrial ablation using bipolar radiofrequency with thermal balloon energy, with no significant difference in pain observed (p <.05). Seven trials evaluated technologies for endometrial polypectomy, of which, 4 compared energy modalities: miniature bipolar electrode resection against resectoscopy (N = 1), morcellation (N = 2), and diode laser resection (N = 1). Two studies compared hysteroscope diameter, and one study compared methods of polyp retrieval. A significant reduction in pain was found using morcellators rather than miniature bipolar electrosurgical devices (p <.001), 22Fr rather than 26Fr resectoscopes (p <.001), and 3.5-mm fiber-optic hysteroscopes with 7Fr forceps rather than 5-mm lens-based hysteroscopes with 5Fr forceps (p <.05). One study investigating septoplasty showed significant reduction in pain when cold mini-scissors, rather than a miniature bipolar electrode, were used (p = .013). Average procedural times ranged from 5 minutes 28 seconds to 22 minutes. The incidence of adverse events was low, and data regarding efficacy and acceptability/satisfaction were limited. Conclusion: Pain is reduced when mechanical technologies such as morcellators and scissors are used compared with electrical devices for removing structural lesions in the office. For hysteroscopic and ablative procedures, smaller and quicker devices are less painful. Large-scale RCTs investigating patient pain and experience with modern operative devices in the office setting are urgently needed.