I Gave Claude Access to My Desktop Outlook Without Touching the Microsoft API

How a 150-line Python script using macOS Accessibility APIs turned my Mac’s Outlook app into a fully AI-readable inbox no OAuth, no permissions headache, no Graph API token. Every few months I try again to get Claude to help me with my emails. Every few months I run into the same wall: Microsoft’s Graph API requires an Azure app registration, an OAuth flow, admin consent for enterprise tenants, and — depending on your company’s IT policy — a support ticket that takes two weeks to resolve. By then, I’ve given up and gone back to manually copy-pasting emails into Claude. Then I found a different angle. macOS has had a powerful accessibility API since the early days of OS X. It’s the same system that screen readers use. Any app running on your Mac including Outlook exposes its entire UI eleme