MS says that in all scenarios this is by design to save the other person's items in the Delegates default folders. This is hard to manage even when managing only 1 other mailbox when the other person's items get mixed in with the Delegate's own emails, but we have delegates that manage multiple mailboxes. You use Outlook 2010 and are a delegate for your manager. An email message that you send on behalf of your manager is saved in your Sent Items folder not His Sent Items folder. MS has provided a hotfix https://support.microsoft.com/kb/2181579, unfortunately this means IT has to touch each Delegate machine to get this setup properly, not a good solution as it should be part of the default Outlook Delegate setup. If you as the delegate create a Draft email (not sent yet) and want to save it in your manager's Draft folder, again to keep the separate, there is no easy way to do that. It automatically saves in the Delegate's Drafts folder by default. We tried moving it from the delegate's folder to the manager's folder, but then the manager does not have access to edit it. So we had to copy it, and then delete the copy from the Delegate's folder. This is crazy as it involved many more steps and is not efficient. If the delegate deletes an item from the manger's mailbox, it once again goes to the Delegates' Deleted Items folder not the manager's Delete Items folder. Again they should be kept separate as it is not the Delegate's email, and the manager should have access to recover it if needed, which he cannot if it is in the Delegate's folder. MS's answer on the last 2scenarios, is to give the manager access to the Delegates Draft & Deleted Items folder. So now the Manager basically has to become a Delegate of the Delegate and the Delegate still has to mix all their stuff with their manager's stuff and the manager then has to wade through all the Delegates stuff too to find his stuff. Absurd!