Outlook and ChatGPT Work Falter as Microsoft Hunts an Authentication Fix

Outlook and ChatGPT Work Falter as Microsoft Hunts an Authentication Fix
Two longtime AI partners faced separate-looking service failures on Monday: Microsoft focused on an authentication fault behind a broad Exchange Online disruption, while OpenAI worked to steady its enterprise ChatGPT Work product amid elevated errors and latency.

The problems emerged late Monday morning, when Outlook and Exchange users began reporting delayed or failed email, mailbox-search trouble, authentication errors and other workflow breakdowns. Microsoft initially said it had confirmed “degraded functionality with various Exchange Online functionalities” and was reviewing diagnostic data to isolate the cause.

The outage grew into a multi-hour test of the business world’s dependence on cloud email. Downdetector reports had passed 5,000 by about 2 p.m. ET, according to one account, and Microsoft was still pursuing a resolution at 5 p.m. The company said it had traced the disruption to an authentication component, developed a remediation strategy and begun testing it on part of its infrastructure. Its later investigation pointed to a possible misconfiguration that prevented authentication components from deploying as expected; Microsoft also said the issue reached beyond Exchange Online.

At roughly the same time, OpenAI said ChatGPT Work had endured elevated errors and latency for about three hours. The enterprise agent, launched in July to help employees build slides, web apps, spreadsheets and documents, left users unable in some cases to begin or continue tasks. “We are continuing work on implementing a mitigation,” OpenAI said.

The overlap was notable because Microsoft has invested heavily in OpenAI, even as the companies increasingly compete. But neither company reported evidence that the incidents were linked. For affected customers, the immediate reality was simpler: core work tools—email on one side, AI assistance on the other—were unreliable for much of the day.

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