Hi @Shaughn Belmore ,
Thank you for posting to Microsoft Community.
Based on your description, I know there is an issue with Outlook connect to account in Exchange Server.
Could you kindly offer the error or screenshot when you cannot connect with me for further assistance?
However, please double check you have configured Internal and External URL in Exchange Server correctly. Ensure all your URIs are updated.
You could refer to Internal and External URL part of Configure mail flow and client access on Exchange servers | Microsoft Learn.
Please check Autodiscover connection for a user by use cmdlet below.
Test-OutlookWebServices -identity: xxxx@example.com –MailboxCredential (Get-Credential)
The cmdlet first checks if it can connect to Autodiscover service and specifies its URL. Then it checks connectivity with all services defined by Autodiscover xml records.
Hope it helps, if there are anything else I could help with, please feel free to contact me.