IPv6 and authentication

I just saw a post over on the mailop mailing list where someone had been bitten by some of the IPv6 email issues I discussed a couple of months ago.
They have dual-stack smarthosts – meaning that their smarthosts have both IPv4 and IPv6 addresses, and will choose one or the other to send mail over. Some domains they send to use Office 365 and opted-in to receiving mail over IPv6, so their smarthosts decided to send that mail preferentially over IPv6.
The mail wasn’t authenticated, so it started bouncing. This is probably going to happen more and more over the next year or so as domain owners increasingly accept mail over IPv6.
If your smarthosts are dual stack, make sure that your workflow authenticates all the mail you send to avoid this sort of delivery issue.
One mistake I’ve seen several companies make is to have solid SPF authentication for all the domains they send – but not for their IPv6 address space. Check that all your SPF records include your IPv6 ranges. While you’re doing that keep in mind that having too many DNS records for SPF can cause problems, and try not too bloat the SPF records you have your customers include.

Related Posts

Authenticating with SPF: -all or ~all

What is SPF?

Sender policy framework (SPF, RFC 7208) is an authentication process that ties the 5321.from (also known as the mail from, envelope from or return path) to authorized sending IP addresses. This authorization is published in a TXT record in DNS. Receivers can check SPF at the beginning of a SMTP transaction, compare the 5321.from domain to the connecting IP address and determine if that IP is authorized to transmit mail.

Read More

SPF Fail: too many DNS lookups

I’ve had a couple folks come to me recently for help troubleshooting SPF failures. The error messages said the SPF record was invalid, but by all checks it was valid.
Eventually, we tracked the issue down to how many include files were in the SPF record.
The SPF specification specifically limits the number of lookups that can happen during a SPF check.

Read More

Four things to check before your next mailing

Like many bits of technology, email is often set-and-forget. Everything is checked and rechecked during setup, and then no one goes back and looks at it again. But mail programs are not static, and people make changes. These changes don’t really break things, but over time they can create their own set of problems.
Setting aside some time every quarter or even every year to check and make sure all the bits of mail are configured correctly is a good idea.

Read More