5 Critical Failures We Hit Shipping a...

Our first enterprise tenant onboarded on a Monday. By Wednesday, 30% of their documents had been silently indexed as empty strings. No error. No exception. The chatbot just said "I don't have enough information", confidently, every time. That was Failure #1. There were four more. Here's the honest account of shipping a multi-tenant RAG chatbot to 500+ enterprise clients — what broke, in what order, and what we should have caught earlier. The System We Built Before the failures, the context. We b