It's a Securities Thing
So I was having this same problem of one-way calendar sync from Outlook to Blackberry, but not Blackberry to Outlook, and after reading about the permissions thing found this to be my problem:
The securities propogating down from my Server to the First Storage Group to my Mailbox Store all had DENY set for the Everybody group and also for some features of the Administrator account.
Perhaps I have opened a security hole, but after removing the DENY parameter, all calendar updates now flow from handheld to Outlook.
Yes, my services were all starting with the Domain Administrator account, but at least in my case this seems to be irrelevant. The problem was in Exchange with the security parameters.
Hope this helps some other poor BES admin out there who got stuck with this problem. Do let me know if this helps.
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