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Sent Items Not Synced between Outlook and Phone

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Exchange 2007 environment.

We see at times an issue where sent items do not sync between devices (i.e. send an email using an exchange account on a mobile device, and it will never appear in sent within Outlook). Most of the time it works, but when it doesn't it can be a bit frustrating to users. As far as I know, none of this is really documented material, but any thoughts on where to start looking/debugging? 


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