In a delegate and manager scenario, when the delegate deletes an e-mail message from the manager’s mailbox using Outlook 2016 for Mac or Outlook for Mac 2011, the delegate receives the following warning dialog:
Are you sure you want to permanently delete the selected message?
If the delegate selects Delete from the popup dialog, the message is permanently deleted from the manager’s mailbox, the item cannot be found in the manager's Deleted Items folder.
This behavior occurs because the delegate does not have write access to the manager’s Deleted Items folder. As a result, the delegate is not able to move the deleted message to the manager’s Deleted Items folder.
To resolve this issue, grant the delegate write access to the manager’s Deleted Items folder. To do this, follow these steps:
In Outlook for Mac, right-click the manager's Deleted Items folder, and select Sharing Permissions.
Click Add User, type the delegate's name, click Find, select the delegate from the list, and then click OK.
Click Permission Level and select Author or a higher permissions level.
The email that was permanently deleted from the manager's mailbox can be recovered from Recover Deleted Items, which can be accessed using OWA or Windows Outlook.