Okay... heres how it works.
If items deleted on the Blackberry device get deleted in Outlook. This means that wireless reconciliation is working. Hold on.... I know what you're thinking...
Here's the deal with making it work the other way around...
(from Outlook to the Blackberry device)
If you empty the "Deleted Items" in Outlook before a wireless reconciliation takes place then the e-mail messages deleted in Outlook will never be automatically deleted on the Blackberry device. They are gone and no longer within the Microsoft Exchange Information Store.
So, how do I ensure that items deleted from Outlook get deleted on the Blackberry?
* DO NOT PERMANENTLY DELETE or EMPTY YOUR DELETED ITEMS IN the OUTLOOK/EXCHANGE MAIL CLIENT until wireless reconciliation has taken place...
If you do, mail in your deleted items will not reconcile on the handheld, they will stay in your handheld device message window. Many people have the option set to "Empty deleted items on exit" in Outlook.
If you do have this option checked, make sure you force a wirless reconciliation before you exit Oulook if you want the items to be deleted on the handheld.
What is the bottom line?
For items to be deleted on the Blackberry device when they are deleted within Outlook they must be in the Outlook "Deleted Items" folder.
Want a sure fire way to test this?
Send yourself a test e-mail message
The message shows up in your Outlook and on your Blackberry.
Now delete the message in Outlook so that it goes into your Deleted Items.
(Do not hold the shift key while pressing the delete key or you will permanently delete the message and therfore bypassing the "Deleted Items."
Wireless reconciliation happens about once every 20 - 30 minutes OR whenever you add, modify, or delete a Calendar, Task, or Address item.
You can always initiate a wireless reconciliation from your Blackberry by pressing the the track wheel while in the message section and selecting "Reconcile Now.
Okay, I get it... but when should I empty the "Deleted Items" in Outlook that I want to go away?
You can empty the deleted items whenever you want.
You can also do it wirelessly from the Blackberry device.
To do this first initiate a wireless reconciliation to ensure that any items in the "Deleted Items" get deleted on your handheld now (by pressing the the track wheel while in the message section and selecting "Reconcile Now. )
As soon as the reconciliation takes place (usually a few seconds) do the following:
Press the track wheel while in the message section and select "Options."
Now scroll down to "Email Reconciliation" and press the track wheel again.
You will see an option that says "Purge Deleted Items." Choose this option.
The Blackberry will prompt you to select "which service to purge deleted items for? DESKTOP or WEB Client
Choose DESKTOP and when it prompts you to find out if you are sure you want to PERMANENTLY remove any items from your deleted items folder on your desktop select YES. (by the way... Make sure you really want to do this because once you delete these they are gone.... or at lease very expensive to recover...)
As soon as you do this the Blackberry device sends a command to the BES server which in turn instructs Exchange to "take out the trash..."
I hope this helps.