A case study in how “AI support” fails the moment it actually matters. This article documents the loss of a critical ChatGPT workspace conversation through backend failure, followed by a support process that denied reality, looped incompetently, and ultimately could not accept its own diagnostic evidence. It exposes systemic fragility, misplaced corporate faith in “Copilot”, and why treating LLMs as reliable infrastructure, especially in regulated environments, is reckless.