Delegate Sent Items go into main sent items instead of Delegate's sent items Outlook 2011

I have outlook 2011 macs running on an exchange 2007 environment.  When a user has another account they are a delegate for they go and send an email from that user.  Upon sending the email, the message is stored in the main user's sent items, not the sent items of the account the email was sent from.  If I add the additional account as an additional exchange account instead of a delegate and send the email, the email appears in the first user's drafts folder instead of the additional account's sent items where it should appear.  This is happening with multiple users and I have verified there are no rules setup that would be causing this.