Introduction: Holmium laser enucleation of the prostate (HoLEP) is a size-independent treatment for benign prostatic hyperplasia (BPH) with durable and excellent long-term outcomes. However, HoLEP is characterized by its steep learning curve. In this video, we introduce the challenges we faced during HoLEP, and describe the steps we took to overcome them. Methods: We obtained the Institutional Review Board approval before conducting our study. From October 2017 to October 2018, we prospectively video-recorded all HoLEP procedures, after obtaining patient's consent, performed at our institution. The cases were managed by a single surgeon (H.E). We used a 100 W Holmium:YAG laser (Lumenis, Yokneam, Israel) with a 550 çm laser fiber. A 28F continuous sheath resectoscope (Karl Storz, Germany) was also utilized. Video clips of the challenges we faced during HoLEP were extracted from the original recordings. The steps we took to address and overcome these difficulties were included in the video. Results: These challenges identified from the recordings include difficulty with positioning the patient, multinodular adenomas, HoLEP after previous BPH surgery, difficult tissue planes, and patients receiving anticoagulant therapy and blood thinners. We also present the obstacles of morcellation in the prostatic fossa, subtrigonal nodules, and the need for perineal urethrostomy. Addressed in this video are patients with urethral strictures before HoLEP, as well as precautions to avoid ureteral injuries. Conclusion: A concern surgeons have about performing HoLEP is the purported steep learning curve. This video attempts to bridge the gap for those performing HoLEP from novice to expert. In this video, we discussed structured techniques to overcome these difficulties, and ways to prevent serious mistakes.