Exchange 2007 outside emails not forwarding to contact SMTP emails

Posted on 2011-09-07
Medium Priority
Last Modified: 2012-05-12
My client has a SBS 2008 with Exchange 2007. I have several GMAIL users who have their emails forwarded via mail contacts which has their gmail email address setup. The server was doing fine with this process untill a couple weeks ago, out of the 5 forwards, 3 still work without a hickup, 1 works with hickups here and there, and 1 does not forward the mail at all.

I believe Exchange is SP2, I have thought about SP3 but ned the down time to do it.. But is was working fine ?

I have setup the Administrator email the same way via mail contact to test, and none of the outside emails reach the contact, and I tried a transport rule, and it still will not reach the contact.

I have tried the system with and without the smart host in place, same thing, no outside mail forwarding. It seems the internal copier machine that sends the scans as emails DOES make it to the mail contacts and Gmail accounts of all 5 users,,I just can't see why the outside emails don't make it thru to the Gmail accounts.

Any Ideas ?

I have seen this work flawless in other setups, why some users making it thru and some don't at all, and some make it thru some of the time, but not all..  Very odd.


Question by:Kevin Caldwell

Expert Comment

ID: 36497216
Try to move the users mailbox in different database who is having the issue.

Expert Comment

ID: 36497906
when you configure smart host, do you set it up to go through a 3 party emal filterring?
if so, check you email filteriing for those users, else
if you remove you smart host, need to check you ISP on how they are treating mail comming out from your public IP.
LVL 61

Expert Comment

by:Cliff Galiher
ID: 36498216
When you say messages aren't forwarding, have you used the message tracking tool in the Exchange console to *verify* whether a message was forwarded? I suspect the most likely cause is not a change on your server, but a change in Google's default spam filters (which, of course each user can still customize, accounting for the discrepency in behavior.) Forwarded mails often have issues with spam filters, as your server is not going to be listed in any SPF record that the outside sender's host may have set up, therefore messages forwarded in such a fashion will rank higher as spam. Common issue,, is inherent in the nature of SPF and how SMTP works, and is not Exchange specific. It also means that, if you verify via message tracking that your messages were sent, there is not much you can do about it on your end to fix the issue.

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Accepted Solution

Kevin Caldwell earned 0 total points
ID: 36498464
We have about 10 users, moving to another database for 1 or 2 users wouldn't be feasible.

The smarthost is the ISP smtp server for mail to go thru for this organization which is a TWTelecom ISP.

Would not the transport rule simply push a copy of the email to the mail contact/smtp email and not look like a forward ?

Author Comment

by:Kevin Caldwell
ID: 36498488
I also can see in the tracking the fail when trying to send to the contact I setup (my cell Verizon Email address) but don't know why it is failing..

Author Closing Comment

by:Kevin Caldwell
ID: 36708047
The only way to get the emails to go to the Gmail was to do a transport rule,, the mailbox forward just would not copy the mail to the Gmail.

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