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Outlook 2010 Search Issues - Emails not found

Hello Experts!

I have several users from different customers that use Outlook 2010 with two different hosting services (gmail and Exchange with Rackspace).   The users are complaining that when they perform a search they don't get any emails found with the criteria.

I tried searching on an email that was the 2nd email listed with the sender's name, "Renae", and the email did not show up in the search, I got no messages found.   However, when I login to the hosted browser version of the email for gmail or exchange/rackspace I can perform a search and the email is found.

What can I do to make the searches work correctly?
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Gregory Miller
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Jackie Man
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Lucas Dawson

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I am still working on this... I don't know if there is any practical limitations of what to expect Outlook to do but this user has 3 Exchange accounts and 3 IMAP accounts and of course tons of email which I would think would have an impact on indexing.  More to come as I trudge through this... oh and of course we have a slow internet connection.
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I think question author has got his solution. Therefore I closed the solution for further commenting. Thanks for all experts for their crucial time.