Every Plone project ends the same way: hundreds of occasional editors, a CMS they touch twice a year, and a PDF manual nobody reads. Training doesn't scale, support tickets pile up for the same three questions, and static documentation is outdated the moment the UI changes. We built a different answer: guided, in-CMS onboarding for Plone 6 and Volto. Instead of digging through a wiki or waiting for a colleague, editors get contextual, step-by-step tours right where they work — the moment they need them, in the exact screen they're stuck on. The real shift is in authoring: tours are recorded by clicking through the actual task, not written by hand — so tours stay cheap enough to update every time the UI changes, instead of rotting like the PDF ever did. Stable selectors are generated automatically. An AI assistant then drafts the step texts from the recorded context, in the editor's own language — while zero page content or user data is sent to the AI provider. This talk walks through the architecture, the hard parts, the privacy-by-design AI integration, and lessons from real editor onboarding — including what changed for editors' confidence and for the support load once tours replaced the manual. Live demo included.