Background/Objectives: This study evaluates the safety and surgical outcomes of performing robotic hysterectomy on uteri weighing over 1000 g, with a focus on the surgeon's learning curve. Methods: A retrospective analysis was conducted on 44 patients who underwent hysterectomy by a single surgeon from January 2020 to February 2024 using the DaVinci Xi System. Surgical procedures included total hysterectomy with bilateral salpingectomy, and specimens were removed via transvaginal manual morcellation. Operative times were segmented into docking, console, morcellation, and conversion times. Results: Results indicated an inflection point in the 20th case, suggesting proficiency after 20 surgeries. Comparison between early (Group A, cases 1-20) and later cases (Group B, cases 21-44) showed significant reductions in console time (CT) and morcellation time (MT) in Group B, leading to a shorter overall operative time (OT). Although estimated blood loss was higher in Group A, it was not statistically significant. Hemoglobin differences were significantly higher in Group B. No significant differences were observed in transfusion rates, postoperative analgesic usage, or complications between the groups. Conclusions: The study concludes that robotic hysterectomy for large uteri is safe and that surgical proficiency improves significantly after 20 cases, enhancing overall outcomes.