Exchange cannot send mail to some domains

Have you encountered that Exchange cannot deliver mail to some destinations on Internet? This is becoming more and more common. You may ask why this happen in the first place and why it’s becoming more common.

The answer lies in how Exchange do DNS queries. Exchange was designed to run on a corporate network where you have full control on how DNS is setup and configured. Basically Exchange believe that DNS will always respond with a correct answer. But when Exchange send mail to Internet, DNS queries and answers might not always be what you expect, this is especially true when more and more organizations start using IPv6.

Using Network Monitor or any other network sniffer when Exchange tries to deliver a mail over Internet you will see that there is query for MX. One problem here is if the destination domain have IPv6 information in their Internet DNS but do not have AAAA records for hosts specified in their MX records, Exchange will simply do not another query for A records for the MX hosts and mail will queue on Exchange.
There are variations on what information is in the destination DNS zone and how your DNS is configured, if you have IPv6 yourself etc, but the behavior is the same, DNS will sometimes fail.

Solution is very simple. configure the sendconnector used for sending mail to Internet to use an external DNS, that is not to reconfigure your windows box to query another name server but simply use the Exchange configuration
Set-SendConnector <SendConnectorNameToInternet> -UseExternalDNSServersEnabled $True

You don’t even have to specify a specific name server on your HUB/Edge server, but you can if you like.

This will change the behavior of Exchange DNS queries to not to stop when there is no AAAA records if other IPv6 information is found, but to continue to do IPv4 DNS queries. remember that Windows prefer IPv6 over IPv4. This can be verified by using a network sniffer.

Have done testing both with HUB and Edge servers and with Exchange 2010 and 2013, and the behavior is the same.

The only reference on Technet on this matter is this article http://technet.microsoft.com/en-us/library/bb676467(v=exchg.150).aspx that talks about normal and lenient mode, but it doesn’t explain the changed behavior if using external DNS or not.

So in short, configure your sendconnectors sending to Internet to use an external DNS to make your live easier.

Looking for Exchange 2013 CU3 ?

look no further other than KB2892464. As usual it contains several bugfixes, support for IE11 in OWA, less memory consumption for the search infrastructure, bug around backup and restore which you can read more about in KB2888315.
To install CU3, you must deploy schema updates so talk with your Active Directory team to have them deployed before you run the CU3 setup.
Download is found here

Microsoft also released Exchange 2010 SP3 UR3 which can be found in KB2891587 and download from here

As always, read the KB and notes carefully before deploy.

happy patching.