The recent OpenAI web crawler incident affecting Triplegangers highlights a critical emerging threat vector that CISOs must address. What began as legitimate AI-driven web scraping effectively became a DDoS attack, with 600 unique IP addresses generating tens of thousands of requests that completely disrupted the target’s operations. The incident revealed how traditional DDoS protection and rate limiting systems may be insufficient against sophisticated AI-powered crawlers. The attack pattern demonstrates the evolving nature of threats, as retail sectors now face an average of 569,884 AI-driven attacks daily, with application-layer DDoS attacks accounting for 30.6% of all AI threats. Successful mitigation required a multi-layered approach, including Cloudflare integration, enhanced robots.txt configuration, and strategic API rate limiting. For CISOs, this incident underscores the need to review and update bot management strategies, implement AI-aware traffic analysis, and enhance monitoring systems to detect unusual scraping patterns. The case serves as a stark reminder that even legitimate AI systems can pose significant operational risks, necessitating updated security architectures and response protocols to protect against both intentional and unintentional AI-driven disruptions.