mail from second exchange server being flagged as spam

40 pts.
Tags:
Exchange 2003
Exchange 2003 Backup
Spam filters
Hello All- I've recently set up a second Exchange 2003 (sp2) server in our domain on a new member server.  The intention is to eventually remove Exchange entirely from the first Win2k3 SBS. The installation went smooth and the transfer of mailboxes off of the first server and onto the second was very smooth and seemless to the end users.  We haven't taken the first Exchange offline yet, though, because we can't tap into the router to change the port forwarding to the new server's IP. The problem I'm now having, though, is that many emails to the outside world are generating underliverable notices and seem to be getting flagged as spam.  I have looked up our IP on mxtoolbox.com to make sure we're not blacklisted.  Why all of a sudden would our emails seem to be spamish now with a second server?  Is there maybe something I missed in the configuration?  I'd like to think that this problem will go away once we take the old Exchange server offline and get mail delivery to/from the new one directly with the correct router port forwarding.  But until then....is there something I need to tweak on the servers themselves?  DNS issue?  Reverse lookup issue?  Relay? Thanks much.
ASKED: November 16, 2009  5:46 PM
UPDATED: November 19, 2009  4:15 PM

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When the new server sends out email, does it go to the public internet from the same IP as the first one? If the DNS names for forward and reverse DNS don’t match you can get black listed that way. (I found this out the hardway.)

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  • Technochic
    Did you add an mx record for your new server?
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  • Crabby117
    No, I didn't think I needed one. Our current MX record on the outside world points to our outside IP address which hasn't changed. The mail domain name hasn't changed either.
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  • Crabby117
    Yes, mail to the public internet comes from the same IP as before the migration. We ended up swapping out the router. Getting a hold of their previous vendor to obtain the password for the old router was just impossible. Seem the old router had "issues" anyway because we also lost POP service as well with no explanation. As soon as we replaced the router, POP service came back and the "spam" problems went away. We forwarded the ports to the new Exchange server and that has been smooth too. We'll take down the old Exchange server in the next couple of days; we're just waiting to see that no more problems arise before we start making changes again. Easier on the troubleshooting process if things stabilize.
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  • MxToolBox
    Definitely want to check to see if your new server was going out the same IP address. You can send a test message to ping@mxtoolbox.com and it will reply back to you your outbound headers with your outbound IP highlighted. Thank you, @MxToolBox
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