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14 June 2008
Email Non-Delivery Due To No Reverse DNS Record
Cause and Solution

Here's the scenario...

You're managing several domains on one IP address (beevis.com, butthead.com, and LakersSuck.com), using host headers with your web server in order to do so successfully. If you're unfamiliar with what "using host headers" means, it's a cryptic way of saying that "whenever a user arrives at your web server, check to see what the URL is and redirect them to the appropriate subdirectory based on that value". In our scenario, you're also managing your own email server, perhaps using something like Smartermail, so each of your domains can have their own email addresses (info@beevis.com, info@butthead.com, info@LakersSuck.com).

The Challenge...

Everything's working great for you. User's are being redirected to the appropriate subdirectories on your web server, and you're sending and receiving emails via each of those email addresses just fine. Oh, wait...SOMETIMES the email you send out doesn't arrive at its destination! A glitch in the system? A random gremlin in the processor? A rogue process? After many hours of re-doing settings, checking settings, system restarts, and hunting for common denominators with your clients, you finally stumble upon the fact that it's mostly only emails going to people who use AOL that are not making it to their destination, along with a few other friends who are using their local cable company for email. You turn on logging and watch for any clues, googling what you find until at last you have distilled things down to their cause: Your domains do not have a reverse DNS record in place. What this means is that an outside system cannot take your IP address and look it up to make sure it's associated with the actual domain that is sending the email.


Here's the clue from the mail server's log file:


"Failed Recipient: blabla@aol.com
Reason: Remote host said: 450 #4.1.3 Relaying temporarily denied. Cannot
resolve PTR record for 208.112.55.164"

Further substantiation from AOL's own site  (http://postmaster.aol.com/guidelines/standards.html) solidifies that this is indeed the issue:
 "AOL's mail servers will reject connections from any IP address that does not have reverse DNS (a PTR record). "

 Whew! At least now you know what's causing this faux random issue! Okay then, let's just add a reverse DNS record for each of our domains so that when a receiving system does their look up, they can see that you really are who you say you are.

The Additional Challenge...

After many MORE hours of attempting to create reverse DNS records (PTR records), you figure out that any given IP address is only allowed to resolve back to a single domain name. So your whole configuration of sharing one IP with several domains has now suddenly become a very bad idea, and it's time to give each its own address.

The Solution...

Tech support provides you with two new IP addresses, which you can see and verify on your Windows system by going to your Control Panel --> Network Connections --> [your connection name] --> Properties -->TCP/IP --> Properties.

Assign each of your domains a new IP address in your web server, then edit your DNS entries for each of those domains to reflect the new IP address. It is quite likely that, if you're using hosting, you will not be able to create your own PTR record and will have to contact your host to do this for you (that is the case with Host My Site), so just make sure you have them do that. After the reverse lookup records are in place, you can verify them by visiting http://remote.12dt.com/lookup.php and typing in the IP address. It should come back with the domain name you assigned to it.

Let everything simmer for 24 hours, just to account for whatever propogation delays and caching are floating around, and give things another whirl. You should be good to go at this point.

Doug out.




Posted by dougboude at 5:58 PM | PRINT THIS POST! |Link | 5 comments
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Re: Email Non-Delivery Due To No Reverse DNS Record
As long as you are on the subject of mail and DNS, be sure to review Sender Policy Framework (SPF) too. If this is not configured or configured improperly, it can negatively effect your ability to send email.
http://www.openspf.org/

Also ensure that you are properly using SENDER and/or FAIL-TO headers so that your outbound mesages don't look like forgeries.
http://www.openspf.org/Best_Practices/Webgenerated
Posted by James Moberg on June 14, 2008 at 11:57 PM

Re: Email Non-Delivery Due To No Reverse DNS Record
I don't think AOL explicitly says they use FCrDNS, I think they only check if a PTR is defined for the IP address. (which is a minimum effort at good policy)
"AOL's mail servers will reject connections from any IP address that does not have reverse DNS (a PTR record)."


A slightly stricter process it to make sure reverse matches forward with FCrDNS.
Name based Virtual Hosts can typically still be used with FCrDNS, the system doing the checking does a look up on the reverse DNS and then does a look up on the returned hostname to verify that it resolves back to the original IP address. So it is possible to have:
vhost1.com ----> IP_ADDRESS ----> mainhost.com ----> IP_ADDRESS
As long as IP_ADDRESS = IP_ADDRESS it will be accepted.

There seems to be a myriad of reasons why email is blocked, and there are a myriad of good ways to resolve the problem. It is a disservice to suggest that every HTTP based website have a unique IP address to send email reliably.
Posted by blech on June 16, 2008 at 4:42 PM

Re: Email Non-Delivery Due To No Reverse DNS Record
@blech, Thanks for the comment. Though I'm not sure how very useful it is since it's somewhat cryptic to "the rest of us" (those of us who don't harbor a special passion for the minute details of the internet's physiology and terminology). As a developer who also has the occasional task of performing some server maintenance type work, all I (and I'm sure a lot of others) really am interested in is the summarized, layman's termed explanation of how to make our frickin email arrive at its destination. I certainly was not purposefully performing a disservice in the information I shared; I was simply sharing it in the hope that someone else down the road who has a similar situation might not have to wade as deep or long through the mire of techno babble muck in order to find what it is they truly need. That having been said, if you can distill your comment down into something a bit more palatable and meaningful for "the rest of us", it would be greatly appreciated! I for one would LOVE to not have to visit this subject again, so doing it completely right the first time is the desired outcome. Anybody out there got a pretty good handle on the whole spam policy inner workings that are being instituted all over the place who wouldn't mind doing a "Email Server Management for Dummies" type post? Something like a checklist of settings to look at and things to do so that one's email server is all set to play properly with the rest of the email servers out there?
Posted by dougboude on June 17, 2008 at 5:16 AM

Re: Email Non-Delivery Due To No Reverse DNS Record
Hi Doug,

I think what blech is saying (and I agree) is that your solution of having a dedicated IP for each domain is overkill. Public IP4 addresses are a scarce resource (which is why we use host-headers and Network Address Translation to share them) and responsible ISPs will normally ask you to justify their use. Needing to use SSL on the domain (because Host Headers won't work over SSL) is a valid reason, but I don't think wanting domain specific ReverseDNS is.

As blech says it should normally be enough that the IP address being used to send mail *has* a reverseDNS/PTR record, not that it necessarily matches the domain. That should satisfy the receiving mail server that the IP address has at least been set up properly on an identifiable network. It's not reasonable to expect every domain to be resolvable back to a unique IP address: there simply aren't enough addresses to go round under IP4.

As James says, having proper a correctly configured SPF record in your domain's DNS and using headers properly are a better way of adding credibility your outgoing mail.

Cheers
Posted by Julian Halliwell on June 18, 2008 at 4:27 AM

Re: Email Non-Delivery Due To No Reverse DNS Record
Wow! I'm excited for you just because I know the pain this was to you and the benefit it is to me! Good job!
Posted by Joe on July 1, 2008 at 2:56 PM

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