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Our mail keeps going into Junk

mikeabc27
mikeabc27 used Ask the Experts™
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Since changing from a peer to peer network with POP3 BT email accounts to an SBS 2008/Exchange 2007 network, many outbound emails are ending up in the recipients junk mail or spam folders.

Our mail is sent directly through SMTP and I've checked our IP address through Reverse DNS Lookup and it resolves OK to remote.ourdomain.co.uk. I've checked the IP against an MXToolbox blacklist check and it's all clear except UCEPROTECT that I can't take seriously.

Any ideas would be appreciated.

 
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How are your emails handled? Was the pop server company the registrar as well? Do they still have your domain but forward your emails to your exchange server?
If you do a mxtoolbox look up is your mx records the same as your reverse dns?
Brian BEE Topic Advisor, Independant Technology Professional

Commented:
How long ago was the change made? It may take time for all server to get the updated rdns information. So they still think you are supposed to be sending from the old location. Hence they flag your mail as junk because the delivery location has changed.

Author

Commented:
How are your emails handled?  Outbound: From SBS server, Inbound: currently by POP3 connector on server to ISP.
Was the pop server company the registrar as well? YES
Do they still have your domain but forward your emails to your exchange server? YES
If you do a mxtoolbox look up is your mx records the same as your reverse dns? Yes, same IP
How long ago was the change made? Six months +
The mail path seems to be a bit off.

If your server is doing a pop3 connector to the ISP, then it sounds like your mx records point to the ISP, which your server then collects instead of emails going directly to your server's external IP.

Wouldn't this mean your mx records point to your ISP which is a different address than your own outgoing IP address?

Author

Commented:
Wouldn't this mean your mx records point to your ISP which is a different address than your own outgoing IP address? That's correct
Hey Mike, it looks like I got two different answers for the same question:

"If you do a mxtoolbox look up is your mx records the same as your reverse dns?" Yes, same IP

"Wouldn't this mean your mx records point to your ISP which is a different address than your own outgoing IP address?" That's correct

If your MX record and your reverse DNS are different, it probably why your email is being flagged as junk.

Author

Commented:
Thanks Jei, below is the setup and obviously where's it's falling down because we're not sending out mail through our ISP, and mail out and mail in are 2 different IPs.
MX record points to BT, the ISP and this mail is downloaded from them to the SBS server.
I created an A record for the SBS server for outbound mail, remote.ourdomain.co.uk using our IP, and this is what I did a Reverse DNS Lookup on.
I thought if this resolved, it would work and not be detected as Junk. Obviously not?
 
Hey Mike. The A record for remote.ourdomain.co.uk  helps for OWA or remote access to email but since your MX record points to a different IP than your reverse DNS this can cause an issue with with people receiving your email.

Before changing your MX record from the IP of your ISP to your external IP address of your exchange server you can try a few things like checking your smtp banner.

Give these two links a read and see if you can try a few things:

http://www.amset.info/exchange/dnsconfig.asp

http://alturl.com/cfdwf
Sorry about that, here are some instructions for Exchange 2007:

http://www.exchangefreaks.com/SMTP-Banner-t138852.html

Author

Commented:
Thanks Jei, as you say the A Record was primarily to set up a GoDaddy certificate for OWA, remote, iPhones connection to Exchange etc.
It didn't click that the different IPs would cause a problem, so long as both were registered properly.
I have to go out now to deal with a problem, but will go through your links properly as soon as I return.
Thanks,
Mike

Author

Commented:
I followed your second of three links and every was set up correctly. When I did the telnet test in the article it checked perfectly.

Author

Commented:
So unsure why it is going into junk mail.

Author

Commented:
OK, even if the send connector is set up correctly, but the sending IP is different to the MX record, could some mail server classify it as JUNK???