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Some email not showing on iPhone but are in Outlook connected to Exchange 2010

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As it says above, I've got a user (yes it is my boss, why doe these things only happen to guys who can influence my pay) where he has an issue where some of his emails just don't show up on his iPhone, but they do in Outlook OWA. 

He's on iOS 7 and connected via Active sync NOT POP or IMAP. Changing to POP or IMAP is not an option. His device is set to sync all and we do have SSL working correctly, he connects happily and I can't see any sync issue. If I do a search I can't find them either, although previously he has had an issue where mail not showing in his inbox was found using a search. I've added removed the account, I really don't want to do that again, he's got a stack of email.

All help much appreciated.


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