Purpose: The present study sought to provide reproducible and patient-oriented metrics to assess the rate of “successful” outcomes (Trifecta) following holmium laser enucleation of the prostate (HoLEP). Clinical and surgical predictors of failure to achieve Trifecta were investigated. Materials and Methods: We queried our prospectively collected database of all patients treated with HoLEP between March 2017 and January 2021. Trifecta was defined as the contemporary presence of: (1) no postoperative complication within 3 months; (2) no urinary incontinence at 3-months follow-up; and (3) 3-month postoperative max flow-rate >15 mL/s. Cases were grouped according to Trifecta achievement. All surgical procedures were carried out by a single surgeon. Surgical experience was divided into two different eras according to the number of procedures conducted (surgical era). Multivariate logistic regression analysis was performed to assess predictors of Trifecta failure. Results: Overall 305 patients were included. Of these, 192 patients (63.0%) achieved Trifecta. Preoperative patient-related features were comparable between the two groups, except for a higher post-void residual (PVR) in non-Trifecta patients (median 180 vs. 130 mL, p=0.003). A significant proportion of Trifecta patients (88.5%) were treated in the second surgical era and in 126 (65.6%) cases an en-bloc enucleation was performed. Multivariate analysis confirmed PVR ≥250 mL, first surgical era and standard three-lobes enucleation technique as independent predictors of Trifecta failure. Conclusions In our experience the rate of “successful” HoLEP, defined according to our newly introduced Trifecta metric, was 63.0%. We demonstrated that surgical strategy together with rising experience and baseline PVR are key elements to forecast the outcomes.