Don't just follow the HOWTO

speakingIconForBlogThere are so many moving parts to ensure good email deliverability. Email marketers need to know marketing, they need to know email and they need to know design. The technical bits of email can be a challenge to learn, and many folks who write tutorials and How-Tos write them for a different audience than marketers.
One of the things I’m trying to do is demystify the technical end of email for marketers. Today I talked about authentication in the Only Influencers newsletter. Check it out!
Understanding the technical: Authentication
Authentication in general

  • Authenticate with both SPF and DKIM. Because they use different mechanisms to authenticate mail it’s unlikely that both will fail at the same time.
  • Some ISPs are checking for authentication alignment even in the absence of a DMARC record. Aligned mail is better than unaligned mail.
  • Hacked DNS records can let a malicious actor take your reputation. Talk to your IT department to use DNSSec.
  • Turning on DMARC affects more than just your bulk mail, it affects all mail coming from your domain. Deploy DMARC policy requests with care or risk deliverability problems.
  • Most receivers request but do not require authentication for mail sent over IPv4.
  • Most receivers require authentication for mail sent over IPv6.

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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.

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Spam, Phish or Malware?

Some mornings I check mail from my phone. This showed up this morning.
PizzaHutMail
My first thought was “oh, no, Pizza Hut is spamming, wonder who sold them my address.”
Then I remembered that iOS is horrible and won’t show you anything other than the Friendly From and maybe it was some weird phishing scheme.
When I got to my real mail client I checked headers, and sure enough, it wasn’t really from Pizza Hut. I’m guessing actually malware, but I don’t have a forensics machine to click the link and I’m not doing it on anything I can’t wipe (and have isolated from the rest of my network).
The frustrating thing for me is that this is an authenticated email. It not from Pizza Hut, the address belongs to some company in France. Apparently, that company has had their systems cracked and malware sent through them. Fully authenticated malware, pretending to be Pizza Hut, and passing authentication on various devices.
Pizza Hut isn’t currently publishing a DMARC record, but in this case, a DMARC record for Pizza Hut wouldn’t matter. None of the email addresses in the headers point to Pizza Hut.
I spent last week listening to a lot of people discussing DMARC and authentication and protecting people from scams and headers. But those all the protocols in the world won’t protect against this kind of thing. Phishing and malware can’t be fixed by technology alone. Even if every domain on the planet published a p=reject policy, mail like this would still get through.
 
 
 

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What to expect in 2016

WttWColorEye_forBlogI don’t always do predictions posts, even though they’re  popular. Most years I skip them because I don’t see major changes in the email space. And, I’m not the type to just write a prediction post just to post a prediction.
This year, though, I do see changes for everyone in the email space. Most of them center on finally having to deal with the technical debt that’s been accumulating over the past few years. I see ISPs and ESPs spending a lot of development effort to cope with the ongoing evolution authentication requirements.
When people started seriously looking at how to authenticate email, the first goal was getting organizations to implement the protocols. This was a practical concession; in order for a new protocol to be used it needs to be widely implemented. Phase one of authenticating email was simply about publishing protocols and getting organizations to use them.
During phase one, the organization that authenticated a mail hasn’t been important. In fact, the SPF spec almost guarantees that the ESP domain is the authenticated domain. In DKIM, the spec says any domain could sign as long as they could publish a public key in that domain’s domainkeys record.
ESPs took full advantage of this and lowered their own development overhead by taking most of the authentication responsibility on themselves. Their domains were in the 5321.from and they published the SPF records. Domains they control were in the d= and they generated and published the DKIM keys. Mail was authenticated without ESP customers having to do much.
We’ve hit the end of phase one. Most of the major players in the email space are authenticating outbound email. Many of the major players are checking authentication on the inbound. Phase one was a success.
We’re now entering phase two, and that changes thing. In phase two, SPF and DKIM are used as the foundation for user visible authentication. Neither SPF nor DKIM were designed to be user visible protocols. To understand what they’re authenticating you have to understand SMTP and email. Even now there are days when I begin talking about one of them and have to take a step back and think hard about what is being authenticated. And I use these things every day!
DMARC is the first of these end user visible protocols built on SPF and DKIM. It uses the established and widespread authentication to validate the user visible from address. This authentication requires that the d= value or the 5321.from address belong belong to the same domain in the visible from address. While you can pick whether the alignment between the visible from and the authentication is “strict” or “relaxed” you have no choice about the alignment.
Prior to DMARC no one really paid much attention to the domain doing the authentication. Authentication was a yes or a no question. If the answer was yes, then receivers could use the authenticated domain to build a reputation. But they weren’t really checking much in the way of who was doing the authentication.
In the push to deploy authentication, ESPs assumed the responsibility for authentication deployed ESPs took the responsibility and did most of the work. For many or most customers, authentication was as simple as clicking a checkbox during deployment. Some ESPs do currently let customers authenticate the mail themselves, but there’s enough overhead in getting that deployed that they often charged extra to cover the costs.
DMARC is rapidly becoming an expectation or even a full on requirement for inbox delivery. In order to authenticate with DMARC, the authenticating domain must be in the same domain space as the visible from. If senders want to use their own domain in the visible from, DNS records have to be present in that domain space. Whether it’s a SPF TXT record or a domainkeys record the email sender customer needs to publish the correct information in DNS. Even now, if you try to authenticate with DKIM through google apps, they require you to publish DNS records.
ESPs aren’t in a situation where they can effectively manage authentication alignment for all their customers. Hosting companies are in even worse shape when it comes to letting customers authenticate email. Developers are facing the fact they need to go back and rework their authentication code. Businesses are facing the fact they need to change their processes so customers can authenticate with DMARC.
It’s not just the infrastructure providers that are facing challenges with authentication. Senders are going to discover they can no longer hand authentication off to their ESPs and not worry about it. They’re going to have to get DNS records published by their own staff.
Getting DNS updates through some big companies is sometimes more difficult than it should be. I had one client a few years ago where getting rDNS changed to something non-generic took over a month. From an IT standpoint, changing DNS should require approvals and proper channels. Marketers may find this new process challenging.
And, if organizations want to publish reject policies for their domains, then they will have to publish records for every outside provider they use. Some of those providers can’t support DMARC alignment right now.
In 2016 a lot of companies will discover their current infrastructure can’t cope with modern authentication requirements. A lot of effort, both in terms of product development and software development, will need to be spent to meet current needs. This means a lot of user visible features will be displaced while the technical debt is paid.
These changes will improve the security and safety of email for everyone. It won’t be very user visible, which will give the impression this was a slow year for email development. Don’t let that fool you, this will be a pivotal year in email.

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