Dear @Bradie Scholz,
Based on my research, it appears that other users have recently reported experiencing the same behavior, and this issue is currently under investigation by Microsoft in certain environments. You can refer to the following Microsoft Support article for details: Users get errors 0x800CCC0E & 0x800CCC0F synchronizing Gmail and Yahoo accounts in classic Outlook
At the moment, you may try the following workaround steps, which have helped some users in similar situations:
Important: The steps below involve editing the Windows Registry. Please proceed carefully, and consider backing up the registry or creating a restore point before making changes.
- Right click the Windows Start Button, select Run, type Regedit and select OK.
- Paste the path below in the Regedit Address Bar and press Enter. Computer\HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Common\Identity\Identities
- Under the Identities key, select each sub key until you find the one that matches the email address that is not syncing.
- Delete the Identities registry key, example in red below. Look for the corresponding Gmail or Yahoo email address, example in purple. That is the identity key in the left column to delete. After you delete the key, restart Outlook and sign in again.
I hope this workaround helps. Please try the steps above and let me know how it goes. Since this forum does not have access to your mailbox or server configuration, we can only provide guidance based on official documentation and community reports.
If Microsoft releases a confirmed fix or update, I’ll be happy to share it here. Please let me know if you need anything else. Have a wonderful day.
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