One of my mobile users reported problems with their Blackberry and Entourage. He was getting some emails, but not others. He would maybe get one, miss two, get 3, miss 1, etc...No apparent rhyme or reason to any of it. What I did: installed updates on my two servers and restarted. They hadn't been offline for almost 3 months until yesterday. Rebooted the firewall. He started to get his missed emails coming in, but his wife (also an employee) reported duplicate emails on her Blackberry. After the reboot, my outlook messages all changed to "read" status and I didn't get emails instantly. I sent myself several test emails and got them hours later, if at all. Our mail has a few jumps along the way to our server. 1. Google Apps for Business Gmail, 2. McAfee email scanner/spam catcher, 3. Our local server. I've had this setup for at least 9 months now and have never had a problem before now. Not sure if updates did more damage-but before the updates we were having problems. I've checked: SMTP Virtual Server, Google/Gmail forwards, McAfee forwards, and Services. Nothing seemed out of place and all seemed to be configured correctly. Please help! I've worked on this for about 12 hours since yesterday and haven't come up with a solution yet.

Does Exchange message tracking show duplicates? Not sure why you are forwarding from Google to an Exchange server however. Seems like a lot can go wrong there. Why not simply accept the messages from the internet directly to the Exchange Server?

I looked through the message tracking center and in one of the messages I sent as a test to myself it shows a duplicate. I'm a novice user-so I had to figure out how to get into the message tracker-but once I did, it all made sense. I knew I had set it up a while back, but never really used it until now-glad I set it up! I'm sure the duplicates mean something... My domain site MX points to google's server, then to McAfee, then to us. I've been wanting to move all users to Gmail, but the higher ups aren't ready to do it yet. It just acts as a catch-all. Never had problems with the setup yet and all the settings seem to still be correct and functioning through my tests.

The duplicate messages are coming from the Google ? If so, there is your culprit.