On Monday, Microsoft 365 broke for roughly a day and a half. It was covered almost everywhere as an Outlook outage. It was also something nobody quite named: the first mass outage of a corporate AI assistant. Microsoft's status page listed Copilot among the affected services, and Copilot prompts needing company data failed while the outage ran.

The model was working the entire time. It just could not reach anything.

In this episode, Stephen Forte covers:

• What actually failed on August 31: within about forty minutes, Microsoft had isolated a failure pattern involving authentication — not email, but the system that proves who you are. It spread to Outlook, SharePoint, OneDrive, Teams, Microsoft's own security product and Copilot, running into a second day.
• Microsoft's stated cause, verbatim: "an issue within a co ...