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Hi @Rob Renna
First, I apologize for this inconvenience, I know this must be affecting your workflow a lot.
Recently, there has been an issue affecting the synchronization of Gmail and Yahoo accounts in Classic Outlook.
Please refer the following document:
Users get errors 0x800CCC0E & 0x800CCC0F synchronizing Gmail and Yahoo accounts in classic Outlook
At the moment, you could try the following workaround steps, which have helped some users in similar situations:
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.
Since this forum does not have access to your mailbox or server configuration, we can only provide guidance based on documentation and community reports. If there are any confirmed updates or official fixes, they will usually be shared through Microsoft documentation or support channels.
I hope this information helps for now.
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