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You can resolve this issue by using one of the following methods.

You have the DelegateSentItemsStyle registry value set to 1.

Your Outlook profile is configured in online mode (not cached Exchange mode).

This problem occurs when all the following conditions are true: When you send an email message from a shared mailbox, the sent email message remains in your Outbox until you manually perform a Send/Receive operation.

Applies to: Outlook 2019, Outlook 2016, Outlook 2013, Microsoft Outlook 2010, Microsoft Office Outlook 2007, Microsoft Office Outlook 2003, Microsoft Business Productivity Online Dedicated, Microsoft Business Productivity Online Suite Federal, Outlook for Office 365.

Email remains in the Outbox when you use the DelegateSentItemsStyle registry value