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Exchange 2003 additional email address doesn't arrive at external destination any more.

Posted on 2007-09-28
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Last Modified: 2008-01-09
I added an additional email address to a user in AD on an Exchange 2003 server. Things went smoothly for a while, then the email (to gmail.com) stop arriving at the Google destination. I've received delivery receipts which stated that the email was delivered and it appears sent. But it never shows up in the person's google inbox. I can successfully send an email from our email server, directly to the recip @ gmail.com, but when that address is used in Exchange AD as a secondary email addy, it only arrives in our internal email and never makes it out to Gmail. No error messages, no failed delivery notifications. But it just doesn't seem to want to share addys in this persons account. I have my own email server, a DNS host and an ISP. As stated, it worked at one time for me. I can successfully send email to this person@gmail.com if I enter the addy manually. But the email never shows up in their external (gmail.com) only in our internal email. Any theories? Any suggestions?
Thanks!
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Question by:foxbyte
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LVL 104

Expert Comment

by:Sembee
ID: 19982581
Does message tracking show the message being sent?
There is a good chance that Google are blocking the traffic as it will appear to be spoofed.

Simon.
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Author Comment

by:foxbyte
ID: 19984545
Simon:
Yes. The message shows as having been delivered. I can even get a delivery receipt on it. But it never apprears in the recipients gmail when I'm trying to send via additional addy in AD email addresses properties. I can send email to the recipient if I manually typing in his gmail addy, however. What's bizarre is this: if Gmail is blocking it from my server as a spoof (and I've contacted my name host and ISP re: SPF and reverse DNS) why would it allow me to send it successfully one way and not the other?
Thanks, Simon. If anything comes to mind...I welcome it.
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LVL 104

Expert Comment

by:Sembee
ID: 19985641
The reason that it is being blocked one way and not the other is because when you send the email directly you are not spoofing.

When the message is forwarded by Exchange, the headers stay almost intact. That can mean the message appears to be coming from another domain.

For example the sender is on Hotmail. Sends to your server, which then forwards it on. The message still appears to come from Hotmail, but not from one of Hotmail's servers.

Automatic forwarding from Exchange is becoming something that doesn't work for many people to many sites for just this reason.

Simon.
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Author Comment

by:foxbyte
ID: 19985699
If I understand you correctly...and I do appreciate your attention on this,...there is no solution exactly. There's an unaddressed flaw in Exchange's auto forwarding? If so, then it's a matter of hoping that Microsoft comes up with a patch or an update to fix it beyond SP2?
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LVL 104

Accepted Solution

by:
Sembee earned 750 total points
ID: 19986665
It is not a flaw in Microsoft's product at all. It is simply another victim of the war on spam.

Most spam is spoofed, because SMTP has no mechanism to prove that the server sending the email message is responsible for the address the message is coming from. There are various techniques to try and deal with that and automatic forwarding of messages gets caught in those techniques.

Other email server products have the same problem. There is nothing for Microsoft to "fix" everyone just needs to change their techniques on how external mailboxes receive email. The ultimate thing will probably be that automatic forwarding dies out or its use becomes very limited, which for me is no bad thing.

Simon.
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