I am sure this has been done but after about 2 days of wasted time researching, I'm just not getting what I need.

What's happening is that we are using Google Apps for our email (MX servers are pointed to GApps) and then I am downloading each user's mailbox (username@domain.net as hosted on GApps) through POP3 connector on SBS 2008 Exchange. I can send email to other domains just fine through our ISP's smart host.

My problem is this: I have setup a user account on SBS for User1 (user1@domain.net) and therefore she has a local mailbox on Exchange. I don't have a user account for Mr. President (president@domain.net) as he wants to continue using IMAP of GApps for his Mac. User1 cannot send any emails to President. But User1 can send emails to any other user with an account on SBS 2008.

I have tried setting the Hub Transport Accepted domain for domain.net to "Internal Relay" while domain.local is set to "Authoritative" and as the default accepted domain.

Exchange gives me this error: The recipient's e-mail address was not found in the recipient's e-mail system. Microsoft Exchange will not try to redeliver this message for you. Please check the e-mail address and try resending this message, or provide the following diagnostic text to your system administrator.

550 5.1.1 RESOLVER.ADR.RecipNotFound; not found

Any ideas as to what this problem is? I would prefer that even mail sent to User1@domain.net be sent through the smart host and then get received by GApps and then get pulled through POP3 for Exchange...

I understand that what I want possibly negates Exchange's purpose and increases bandwidth requirements, but my business case for this is IF exchange were to fail, we will have ALL our inbox intact on Google Apps. And of course, if there were a virus sent from one of our workstations, it would be better if it passes through Google Apps first before it gets to Exchange (whereas in the default configuration, it just sends it directly to the Exchange mailbox and never goes through the internet).


@Jared: I don't mean any disrespect but honestly I don't know why companies bother to pay for and use Exchange at all if they're not going to use it the way it's intended. You've got a configuration that is more cumbersome to setup, manage and troubleshoot, all under the guise that you're "protecting" yourself from some unforeseen future failure that in all likelihood isn't going to happen. If you don't trust Exchange, or the server, or your internal infrastructure or yourself then get rid of Exchange completely and stop flogging yourself with this unsustainable scenario.

I know that the POP connector comes from MS but I think it was a bad idea on their part as it gave companies a reason to implement scenarios like you have, which in my opinion, are more trouble than they're worth.

Have you considered bringing your email "fully" in house and doing away with the current implementation? You'd make administration a lot easier and you can always build in the required level of redundancy and availability.

You've spent 2 days looking for a solution to a problem that wouldn't exist if you were using Exchange the way it was intended to be used. All of the reasons you stated for implementing this scenario can be addressed internally.

  • Yes I have realized this and have thought about this for the most part. The problem is with REALLY high turn over rates for this company, combined with ZERO budget for IT (make do with what we already have) then this is the best that I can see. "merging" old email accounts to a new user's email account is a pain using Outlook 2007 with POP. In exchange it's just drag and drop and it will follow you. – Jared Jul 1 '11 at 4:13
  • Also, I believe that having our mail hosted in Google Apps is more secure as their spam/virus filtering is WAY WAY better than we can ever get with the built-in ForeFront for Exchange Server setup. I am not making any excuses. It's just an issue of budget for IT. I'm a one man shop here and If my boss would follow my recommendation to stick to outlook, then we won't have problems. But then again, he is the president and he owns the company so he gets what he wants and that is everyone on Exchange while him on GApps IMAP for his apple devices. Sucks for me, I know. – Jared Jul 1 '11 at 4:16
  • I get it. I have a boss who is very similar. As for the "security" of your email in Google Apps, you could always use Postini with your Exchange server (which is owned by Google and is probably what they use for Google Apps). Postini is about $1.00 a month per user for their Silver level service. – joeqwerty Jul 1 '11 at 4:20
  • You could also switch to hosted Exchange which would give you the external security and availability that you need but allow you to do away with trying to get 2 separate email systems to work together. – joeqwerty Jul 1 '11 at 4:24
  • I'm afraid that's not possible. This boss does not want to pay recurring fees (aside from electricity and domain name). The point he's making is that SBS2008 has exchange and sharepoint, this and that. Make it all work together as it was intended to while having a "real-time" backup and "screener" for mail. I have no qualms about that other than it makes it complex (but very reliable). I also do not trust my users with email especially spam mail that gets in once in a while through Google Apps. I just want this to work so I can move on to other things like Spiceworks or Nagios for NMS – Jared Jul 1 '11 at 4:28

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