With Outlook versions before 2010, you were limited to having 1 Exchange Type Account (mailbox) per profile. In this case, adding additional mailboxes was handled exclusively through the “add additional mailbox” option in the exchange account settings. However, this would only work if both accounts existed on the same exchange organization.

Beginning with Outlook 2010, you are now allowed to add multiple exchange accounts, this solves the problem of having multiple exchange accounts, on different organizations. However, adding multiple delegate email addresses for each exchange account now becomes a problem. Adding additional or delegate mailboxes for the first exchange account that was added in the profile works fine, however the “add” button in the additional exchange accounts is grayed out or disabled.  Here is a solution courtesy of http://www.msoutlook.info and Microsoft

1. http://www.msoutlook.info/question/756

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Are you responsible for multiple exchange (e-mail) mailboxes? Tired of sent items not going into their corresponding sent-box? Here is the solution for Microsoft Outlook

Email that you send on behalf of someone is not saved in their Sent Items folder

From: http://support.microsoft.com/kb/2181579

This also works in newer versions of Outlook, just locate the appropriate registry key version.  Microsoft FixIt will also make the changes for you locally