Hi @J-3804 ,
What's the version of the affected Outlook client? You can view the version information via File > Office Account > About Outlook.
Is there any error message when the issue occurs?
Agree with Manu that it's recommended to use the I need help setting up my Office 365 email in Outlook diagnostic in the Support and Recovery Assistant (SaRA). The tool can automatically help check and return possible solutions for you to use to try to fix any detected issues.
Besides, the issue may also caused by local network configuration issues, so it's suggested to verify port 443 is open and network proxy configuration is not redirecting clients to one particular Microsoft 365 IP address range or URL. For more details, you may refer to Outlook can't connect to Exchange Online or a user can't create new Outlook profiles in Microsoft 365.
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