• Purpose: To estimate the prevalence of untoward events during cataract surgery with the use of pupillary expansion devices and intraoperative floppy iris (IFIS). • Design: Retrospective analysis of 4923 cataract surgery cases from the Veterans Affairs Ophthalmic Surgical Outcomes Data Project. • Methods: Outcomes from 5 Veterans Affairs medical centers were analyzed, including use of alpha-blockers (both selective and nonselective), IFIS, intraoperative iris trauma, intraoperative iris prolapse, posterior capsular tear, anterior capsule tear, intraoperative vitreous prolapse, and use of pupillary expansion devices. P values were calculated using the χ2 test. • Results: A total of 1254 patients (25.5%) took alpha-blockers preoperatively (selective, 587; nonselective, 627; both, 40). Of these 1254 patients, 428 patients (34.1%) had documented IFIS. However, 75.2% of patients with IFIS (428/569) had taken alpha-blockers preoperatively (P <.00001). A total of 430 patients (8.7%) had a pupillary expansion device used during their cataract surgery, of which 186 patients (43.4%) had IFIS (P <.0001). Eighty-six patients with IFIS had at least 1 intraoperative complication and 39 patients with IFIS had more than 1 intraoperative complication (P <.001). • Conclusions: The use of either selective or nonselective alpha-Antagonists preoperatively demonstrated a significant risk of IFIS. Nonselective alpha-Antagonists caused IFIS at a higher prevalence than previously reported. This study did demonstrate statistically significant increased odds of surgical complications in patients with IFIS vs those without IFIS in all groups (those taking selective and nonselective alpha-Antagonists and also those not taking medications).