Try Resolution for Cause 2 & 3 from below article.
http://www.blackberry.com/
Main Topics
Browse All TopicsWe 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!
This Question has been solved and asker verified All Experts Exchange premium technology solutions are available to subscription members.
Experts Exchange has been collecting answers to technology questions since 1996…3 million and counting! If you have a question, chances are we already have your answer.
If you can't find the exact answer you're looking for, ask our exclusive community of 50,000 experts. You’ll get a personalized answer from a trusted professional.
Thousands of free tech tips, tricks, how-to’s and tutorials are available in our peer reviewed articles section. See for yourself how smart our experts are, no login required.
Access the answers to your technology questions today.
30-day free trial. Register in 60 seconds.
Members of the expert community talk about why the experience at Experts Exchange is different than what you will find anywhere else.

Try it out and discover for yourself.
30-day free trial. Register in 60 seconds.
Join the community of experts here and help other tech pros by answering question in your area of expertise. You can earn FREE access to all Experts Exchange's premium features and resources.
Try Resolution for Cause 2 & 3 from below article.
http://www.blackberry.com/
That is an ususal problem and it is known as Hard Delete.
Just follow up this article and to as it says.
http://coreygilmore.com/bl
Regards
Hi, I would recommend upgrading the users firmware if an update is available (see link below). Any firmware version below 4.6.0.210 has a number of issues that can cause these type of issues.
You can check your current firmware version by going to Options > About > Third line.
http://na.blackberry.com/e
Business Accounts
Answer for Membership
by: jderaPosted on 2009-05-15 at 17:42:10ID: 24400647
First thing to do is resend the service book from BES. If after 20 minutes that has not solved the problem. Then on bb device go to Options > Advanced Options > Service Book. Delete all the entries, not all will delete and you will have to delete them one by one. Then go to BES resend the service book again. Wait 20 minutes and test. If that fails then remove the user completely from BES and restart activation.