Hi @jojothehumanmonkey ,
Welcome to our forum!
Do you mean that you can't configure your account as IMAP or Exchange in Outlook 2021?
If so, what's the version of your Outlook 2021? (File > Office Account > About Outlook). Please make sure you have upgraded your Outlook to the latest version.
Have you tried to add another account for test?
And does this issue occur with other users in your organization?
According to your description, "keeps asking for email and password over and over again", as I know, we can run diagnostics to determine the issue that might cause the error. For more information, please refer to: Run a self-diagnostics tool.
In addition, based on my experience, Outlook password prompt issue will be affected by many factors, such as incorrect cached credentials, corrupted account settings and so on. Please refer to this article and try the suggestions about the issue to check if there're any differences: Why does Outlook keep prompting for password.
Hope the above help!
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