Hello Jamie Penistone
Good day! Thank you for posting to Microsoft Community. We are happy to help you.
Regarding your post, as many users facing this query, so suggest you to check with one of the affected users to check with scan Outlook with SARA tool by follow the steps mention in Scan by using Microsoft Support and Recovery Assistant - Outlook | Microsoft Docs. The Microsoft Support and Recovery Assistant (SaRA) uses advanced diagnostics to report known problems and details about your Microsoft Outlook configuration. Additional choose Outlook from SARA tool and select Outlook keeps saying "Trying to connect..." or "Disconnected" option and check the result. To learn about SARA tool, kinldy check details from About the Microsoft Support and Recovery Assistant.
For testing purpose, ask one of the affected user to configure his Outlook in different system with different network (not belongs to your organization’s system) and check if it makes any difference.
Further during search, found one of the know issue with connectivity, so kinldy check details from Internet connectivity issues in M365 apps after a change to the IP address range (microsoft.com) to see if it match with your situation.
Thank you so much for your precious time and cooperation. Stay safe and healthy.
Sincerely,
Ankita Vaidya | Microsoft Community Moderator