Who Moved My Settings? Automating Vendor Doc Drift Detection

Spencer Johnson's Who Moved My Cheese? is about adapting when things change around you. In cloud security compliance, the cheese moves constantly. Microsoft renames a menu. Google moves a toggle to a different admin panel. Your carefully written implementation guide now points to a screen that no longer exists. Your client follows the old steps and hits a dead end. We built an automated pipeline that crawls vendor documentation weekly, compares it against our internal implementation guides, and flags meaningful drift: renamed UI paths, deprecated features, relocated settings. It runs on Cloudflare Workers with a Durable Workflow, uses Claude for semantic analysis, and costs about 50 cents a week at scale. Here's how. The Problem: Documentation Drift We maintain implementation guides for security controls, such as "Enable MFA for Admin Accounts in Microsoft Entra" or "Configure Conditional Access Policies." Each guide has specific, click-by-click instructions referencing particular admi