Last week, Cliffside Cybersecurity, a Microsoft partner, stopped using ChatGPT because it no longer met business requirements and moved to Copilot for ecosystem integration. Three benefits emerged: improved comfort with documentation via native cloud features in Word and Excel, sharper documentation production, and one less vendor to manage. The move surfaced five unanticipated risks. First, data portability: years of prompts, custom instructions, and project history were locked in the old platform, with thin export options, forcing a hard call to leave much knowledge behind. Second, maintenance of AI-built solutions: when employees leave, documentation and support ownership for fast-built solutions may be missing, requiring standard IT hygiene like a "how this works" doc, a named owner, and a review date, with code committed to git where possible. Third, laptops are the new servers: the company discovered several business-important solutions—scripts, custom agents, scheduled jobs—running on individual laptops, backed up only by hope, representing sanctioned shadow IT in reverse. The article implies two additional risks, but the body text cuts off before detailing them.