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When a user searches in outlook some emails do not show up.

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We have been working on this for quite some time.  One user, when they try to search in Outlook 2010 or OWA 2007 there will be some emails that do not show up in the search results, even though they are in their inbox.  We have repaired his local outlook profile, recreated his account on his computer, created his account on a new computer.  Tried searching with Outlook indexing turned both on and off, and when on it did say indexing complete.  Search in OWA returns the same results, as does searching his inbox when added as a separate mailbox to another account.  Any help or ideas would be appreciated.  We are running Microsoft Office 2010, Windows 7 Enterprise and Exchange 2007.

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