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Blackberry Bold with Blackberry Enterprise Server sync with Exchange 2007

We have a user who has a Blackberry Bold. We use Blackberry Enterprise Server with Blackberry Manager v. 4.1.6.9. Users are set to sync with Exchange 2007 and their Outlook 2007 software. One user is able to sync bidirectional with everything except for when he deletes an email in his Outlook it does not sync with his BB Bold. If you push reconcile now on the Blackberry it will delete the email but will not do it automatically no matter how long you wait. The Email Reconciliation options on the blackberry are set to delete on handheld and desktop, wireless reconcile is on, on conflicts mobile wins. Everything under PIM sync on the BES is bidirectional server wins except for Certificate summary data. Any help with this is greatly appreciated, Thanks!
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jdera

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AllCounty

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Thank you for your comments and possible solutions, I'm going to wait until this user comes back later in the week to try what was mentioned
That is fine, but check my comment on your server first, for that you do not need the user.

By the way what is your mobile network carrier?

Regards
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Thank you everyone for posting your responses, unfortunately none of the solutions worked, a few hours with the phone service provider and blackberry and no answer either, we ended up replacing his blackberry.
Thanks