Background <p>To evaluate whether lateral lobe enucleation time is associated with postoperative urethral stricture after holmium laser enucleation of the prostate (HoLEP).</p> Methods <p>We retrospectively reviewed 519 HoLEP procedures performed between January 2023 and January 2025. To minimize operator- and technique-related heterogeneity, we included only standardized trilobar HoLEP cases performed by a single high-volume surgeon (&gt; 400 prior cases); procedures by other surgeons and/or non-trilobar approaches were excluded. Urethral stricture was defined as symptomatic urethral narrowing confirmed endoscopically. The prespecified exposure was total lateral lobe enucleation time (sum of both lateral lobes), modeled per 10-minute increase. Associations were evaluated using Firth bias-reduced logistic regression.</p> Results <p>Among 168 eligible patients, 8 (4.8%) developed urethral stricture. Total lateral lobe enucleation time was longer in the stricture group (median 70.0 [IQR, 53.0–70.0] vs. 32.5 [IQR, 26.0–45.2] minutes; <i>p</i> = 0.017). Follow-up duration differed between groups (<i>p</i> = 0.002). In multivariable Firth regression adjusting for age (per 10 years), prostate volume (per 10&#xa0;g), and preoperative urethral catheterization, lateral lobe enucleation time remained independently associated with stricture (adjusted OR, 1.78 per 10&#xa0;min; 95% CI, 1.24–2.53; <i>p</i> = 0.002). Preoperative urethral catheterization was also associated (adjusted OR, 4.48; 95% CI, 1.03–19.50; <i>p</i> = 0.045).</p> Conclusions <p>Longer total lateral lobe enucleation time is independently associated with urethral stricture after HoLEP and may be related to increased instrument angulation and mechanical stress at the urethral fulcrum.</p>