Symptoms
Consider the following scenario:
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You access a Microsoft Exchange Server 2010 mailbox by using Microsoft Office Outlook 2007 that has the Exchange email account configured in online mode.
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The Outlook 2007 client has an additional transport or email account in the Outlook profile, such as POP, IMAP or Live Meeting Transport.
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You send a deferred delivery email message.
In this scenario, the email message is not delivered, and remains in the Outbox folder.
Resolution
To resolve this issue, install the following update rollup:
2579150 Description of Update Rollup 4 for Exchange Server 2010 Service Pack 1
Status
Microsoft has confirmed that this is a problem in the Microsoft products that are listed in the "Applies to" section.