Background: Pelvic organ prolapse is a common condition of pelvic floor dysfunction in women, especially in adult vaginally parous and elderly women. Because of its anatomy, the anterior compartment has a significant effect on urinary symptoms. Anterior colporrhaphy and colpocleisis are major anterior compartment prolapse-related surgeries. As we know, postoperative urinary retention (POUR) is one of the most common complications following pelvic floor surgery. To prevent this complication, indwelling bladder catheterization is routinely applied. In contrast, to minimize risk of infection and the patient’s discomfort, the catheter should be removed as soon as possible. However, there is a lack of clarity regarding the optimal timing for catheter removal. Therefore, the aim of this trial is to compare the rate of POUR after anterior prolapse surgery between early transurethral catheter removal (24 h postoperatively) and our standard practice (on postoperative day 3). Methods: We conducted a randomized controlled trial among patients undergoing anterior compartment prolapse surgery between 2020 and 2021 at a university hospital. Women were randomized into two groups. After removal, if the second void residual urine volume exceeded 150 mL, POUR was diagnosed, and intermittent catheterization was performed. The primary outcome was the POUR rate. The secondary outcomes included urinary tract infection, asymptomatic bacteriuria, time to ambulation, time to spontaneous voiding, length of hospitalization, and patient satisfaction. Analysis was performed according to the intention to treat principle. The calculated sample size was 68 patients (34 patients in each group) for a 95% confidence interval, 80% power, 5% probability of type I error, and 10% data loss. Discussion: This study demonstrated that early catheter removal was comparable in POUR rate to conventional treatment with shorter hospitalization among patients undergoing anterior compartment prolapse surgery. Additionally, we observed no re-hospitalization owing to POUR. Therefore, early transurethral catheter removal is preferable following anterior compartment prolapse-related surgery.