Best practices for the "Delegate can see my private items" feature

When setting up a delegate, there is an option to allow the delegate to see your items marked as private.

 

Here's 3 simple steps to get a consistent behavior for your managers and delegates who rely on this feature.

1. Don't use Outlook Web App to view private items.  As of Exchange 2010, this doesn't seem to work.
2. Be sure the delegate and manager are using the same version of Outlook, including patch level
3. Add the manager's mailbox as an additional mailbox for the delegate's profile go to account settings, change, more settings, advanced tab, Add... Open these additional mailboxes

 

Here's a collection of public articles that can affect this feature:

• http://support.microsoft.com/default.aspx?scid=kb;EN-US;2597011 This is cumulative update for Outlook 2010 that fixes the following issue:
  Consider the following scenario:
  • User A adds user B as a delegate of user A in Outlook 2010.
  • User A enables the Delegate can see my private items setting.
  • User A creates a private appointment item in the calendar.
  • User B logs on to user A’s mailbox and can see the private appointment item.
  • User A removes user B as a delegate of user A.
    In this scenario, user B can still see the private appointment item