What a week! Switching hosting providers, setting up a new content management system for this blog (more on that as soon as it’s ready) and all at the same time as suffering e-mail problems as, since the middle of the week, every e-mail that I’ve sent to a particular contact has bounced back with the following message:

This is an automatically generated Delivery Status Notification.

Delivery to the following recipients failed.

someone@somewhere.net

Reporting-MTA: dns;mymailserver.markwilson.co.uk

Final-Recipient: rfc822;someone@somewhere.net
Action: failed
Status: 5.5.0
Diagnostic-Code: smtp;550-Verification failed for <myalias@markwilson.co.uk>
550-No Such User Here
550 Sender verify failed

I have various anti-spam measures on my mail server, but this appeared to be a problem when sending mail to a particular external host – e-mail sent to the same contact via a different mail server was received with no problems.

I set about researching the 550 Sender verify failed message and found various suggestions as to what might cause such an error – the most useful of which was a message on a newsgroup post which suggested it may be caused by an incorrect reverse DNS (PTR) record (thanks to Ben Winzenz for replying to that group a couple of years ago).

Even though much of my mail was being delivered successfully, that seemed like a perfectly reasonable explanation – the reverse lookup for my IP address would have returned a hostname in the format username.myisp.co.uk, rather than mymailserver.markwilson.co.uk (as confirmed by a DNS report on my domain, which also commented that “RFC1912 2.1 says you should have a reverse DNS for all your mail servers. It is strongly urged that you have them, as many mailservers will not accept mail from mailservers with no reverse DNS entry”), so I set about getting the record updated by my ISP (it has to be done by the owner of the IP address block).

Initially I asked my ISP to add my mail server’s DNS name as a second PTR record for my IP address but in practice I found that DNS responded in a round robin pattern (rather than returning all the matching records) so I couldn’t rely on a consistent response and was still experiencing mail delivery failures. Finally, after reverting to a single PTR record for my IP address and waiting for DNS propagation (again), I was able to successfully send e-mail to the contact with whom I’d previously experienced issues (phew!).

As more and more hosts take action to prevent unsolicited commercial e-mail (UCE – also known as spam), this is likely to be a more common occurrence and it just underlines how important a correct DNS configuration is.