From one newbie to another, here is my .02 cents.
If he is using Blackberry Internet Service, there is no way to delete emails out of Outlook from the blackberry (unless Redirector does it). He would have to do it manually just like you are manually deleting email from the blackberry.
But, there is a work-around. I also use Outlook and have turned off the "automatically send/receive email every XXX minutes" feature. This way, when I vew email on the blackberry and want to delete it entirely, I select delete, On Mailbox and Handheld. Then when I manually click send/receive in outlook those messages are no longer on the email server and therefore does not show up in Outlook.
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