Question re Exchange Server 2003 SP2 and why my outbound emails are getting delayed delivery reports or spammed by recipients

Posted on 2006-10-23
Medium Priority
Last Modified: 2010-03-06
Hi guys. I've just installed SBS2003 R2 so I am running Exchange 2003 Sp2. Prior to this was using Outlook 2003 as a pop3 client and using ISP SMTP to send emails to all our customers. Am really happy overall but ....

a) some (only a few) customers since we changed to Exchange say that our email to them is either always or intermittently getting put into their spam system. My question would be that our sending email address is the same so why would this be? Is it because in some subtle way Exchange delivery is different from the old ISP way?
b) perhaps related to the above. I am getting  more of the following delayed delivery reports eg;
This is an automatically generated Delivery Status Notification.



Delivery to the following recipients has been delayed.


My question here is; is this possibly an indication that our email to them is being treated as spam also? I though that all spam engines either rejected or accepted email, but is there a possiblity they might 'ignore' it thus triggering these delayed delivery reports?

Any help on these probably linked questions would be much appreciated!
Question by:MPSmith4258
  • 2
LVL 39

Accepted Solution

redseatechnologies earned 2000 total points
ID: 17793768
Hi MPSmith4258,


a) previously your email was going via your ISP, it is now (probably) going direct from your server - which some accounts do not like.  The solution is to use an SMTP connector with a smarthost to route mail via your ISPs mail relay server


b) possibly related to the above, probably not.  Either way, the solution to A will be the solution to this as well (as it totally changes the way you send mail.

Hope that helps,


Author Comment

ID: 17793973
Thanks Red, I suspected it might be something like this. Only downside of this solution for me is I occasionally switch from one of my two broadband lines to the other, and both are on different ISPs.. so I'll need to have two connectors and swap between them when I do this ...
I'll monitor how bad the problem is for a while before implementing this solution ... most of the problem customers are able to either themselves, or through their IT dept, add us to trusted senders lists.
Thks again
LVL 39

Expert Comment

ID: 17793994
No problems,

As far as switching between 2 ISPs, that is going to be tricky - all you will really need to do is open up the connector and change the smart host to the other ISPs mail server

Good luck with it, and let me know if you have problems


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