I'm running a dual delivery Google Apps setup right now where Google Apps is the primary mail server by my domain's MX records. My users can use either Exchange or Google Apps until we phase out Exchange.

I've set Google Apps to forward all mail to Exchange inboxes. However, when my users use OWA or Outlook to send mail from Exchange to another domain user, Exchange internally routes the email to that other user's Exchange mailbox, completely skipping Google Apps.

It would be simple to set Exchange to forward sent and received messages to Google Apps on a per-user basis, but this would lead to a mail loop where Exchange and Apps sent each other the same message forever. I just want to forward sent messages to Google Apps and the Exchange inbox.

So, I tried setting up another receive connector. This didn't do anything, so I suspect that "internal" email processing takes place before "external" mail processing or send connector rules can be applied. This Microsoft page explains how emails are routed but offers little guidance about how to force internal domain messages to be delivered/forwarded externally using MX records, which would solve my problem.

Has anyone else had this problem? Am I approaching the problem correctly? This seems like a fairly common function in a mail server, but I can't seem to find it.


Something similar came up in this question, and I wanted to mention something I left out of my comments there:

This is a fundamentally kludgy thing to do, and no matter what you come up to make it sort-of work, it's gonna be a kludge.

You're taking two mail systems, setting them up as if they're the mail system for yourdomain.com, and then trying to get them to talk to each other using mechanisms that are intended for moving messages around between different email domains. Of course there are problems! (Don't take this personally, BTW, I've had to do it in the past, albeit on a more limited basis.)

One kludgy idea: I don't use Google Apps, can you set it up to receive email for another domain (yourdomain.net or temp.yourdomain.com) and deliver those messages to the same mailboxes? i.e. ugly@yourdomain.com and ugly@temp.yourdomian.com both go to the same user's mailbox? Then Exchange can copy any sent messages to that new domain. The ugly part with this setup or many variations of it is that people will get a copy of any "Sent" messages in their Inboxes.

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