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Mailbox Search Returning Incomplete Results

Hi,

We have one user with a very large mailbox (11GB), when searching for specific e-mails using either Outlook 2013 or OWA the results are incomplete.
For example;  the mailbox contains e-mails from Joe Bloggs going back to 2008,  if I search for a message "from: Joe Bloggs" I see the following:
In Outlook 2013 - oldest search result is June 2014 (I am clicking to show More at the bottom of the search results)
In OWA - oldest search result is January 2014. On the left "Show these messages" is set to All. If I change this to "Older than a year" the oldest message is from December 2012.

So far I've tried:
Outlook in cached mode and in online mode, rebuilding the search index
In Exchange I've tried moving the user's mailbox to a different database. I've also tried activating the database on the other server in the DAG.

Running Test-ExchangeSearch -Identity joebloggs@contoso.com finds a result. Any ideas on how to troubleshoot this? Thanks


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