Our study aimed to assess the efficacy and durability of holmium laser enucleation of the prostate (HoLEP) in managing acute urinary retention (AUR), neurogenic chronic urinary retention (NCUR), and non-neurogenic chronic urinary retention (NNCUR). We also sought to compare outcomes in patients with preoperative urinary retention (UR) to those without. We conducted a retrospective analysis using prospectively gathered data from men who underwent HoLEP at our institution between October 2017 and July 2022. Patient demographics and outcome measures were recorded, including indications for the procedure, median urinary volume drained, or median postvoid residual urine volume (PVR) before catheterization or HoLEP. Chronic urinary retention (CUR) was defined as PVR >300 mL in males able to void; and initial catheter drainage >1000 mL in males unable to void, in the absence of pain. NCUR and NNCUR were differentiated based on the presence of any significant illness or injury with a neurologic impact on the bladder. All patients had postoperative followup visits at one, three, six, and 12 months. Our evaluation included the International Prostate Symptom Score (IPSS), quality of life (QoL) assessment, maximum urinary flow rate (Qmax), PVR, and catheter-free status. Three hundred sixty-eight males who underwent HoLEP were included in our study. The UR group consisted of 189 patients (70 AUR, 42 NCUR, and 77 NNCUR), and the lower urinary tract symptoms (LUTS) group was comprised of 179 individuals. There were no statistically significant differences between the NCUR and NNCUR subgroups regarding demographics and outcomes. At 12 months postoperative, the AUR group had a higher catheter-free rate than the CUR group (p=0.04), and other outcome variables were comparable between the two cohorts. The UR group had a significantly lower QoL score at one month (p=0.01) and a significantly lower IPSS score at one and 12 months (p=0.034 and p=0.018, respectively) than the LUTS cohort. During all followup visits, the UR group had a significantly higher PVR than the LUTS cohort. The successful first trial of void (TOV) rate for the UR and LUTS groups was 81% and 83.2%, respectively. At 12 months postoperative, the catheter-free rate for the UR and LUTS cohorts was 96.3% and 99.4%, respectively. HoLEP is an effective and durable treatment for UR with a high catheter-free rate and comparable outcomes when performed to manage LUTS.