Gap Inc.’s new customer-facing chatbot briefly veered into off-topic and inappropriate territory after what AI startup Sierra described as a coordinated jailbreak attempt by a “bad actor.” Sierra said a misconfigured guardrail allowed the Gap agent to slip past its abuse-detection system. The incident was first reported by The Information. CCB Journal published this account on 5 December 2025. A report is an account of what happened, not a finding of fault.