By Connor Jones
Publication Date: 2026-06-15 15:33:00
Security
Connectivity checker trips browser alarms thanks to lapsed security paperwork
Microsoft appears to have dropped the ball with its certificate management after a domain used by sysadmins worldwide to test connectivity to Microsoft 365 started throwing untrusted connection warnings in browsers.
The connectivity.office.com domain is used by IT pros to test their network’s connectivity to Microsoft 365 and ensure their firewalls aren’t blocking anything that could affect an organization’s access to Microsoft servers.
An SSL server report retrieved on Monday showed that the certificate expired on June 14 after last being renewed on December 16, 2025.
At the time of writing, 35 hours have passed since the certificate expired, and Microsoft has still not renewed it, despite many in the IT community making their opinions on the matter known.
Certificate renewals are often automated in this day and age, but…
