February 2016: The Month in Email

Happy March! Here’s a look back at our last month of email adventures.
Feb2016forBlogIt was a busy few weeks for us with the M3AAWG meeting in San Francisco. We saw lots of old friends and met many new people — all in all, a success, despite the M3AAWG plague we both contracted. Hot topics at the conference included DMARC, of course, and I took the opportunity to write up a guide to help you determine if you should publish a DMARC policy.
On the subject of advice and guidance, Ask Laura continues to be a popular column — we’ve had lots of interesting questions, and are always looking for more general questions about email delivery. We can’t tackle specifics about your program in this column (get in touch if we can help you with that directly) but we can help with questions like “Will our ESP kick us off for mailing purchasers?” or “Help! I’m confused about authentication.”
Continuing on the authentication front, I noted that Gmail is starting to roll out some UI to indicate authentication status to users. It will be interesting to see if that starts to affect user (or sender) behavior in any way. In other interesting industry news, Microsoft has implemented an Office 365 IP Delisting page. I also wrote a followup post to my 2015 overview of the state of ESPs and purchased lists — it’s worth checking out if this is something your business considers.
I wrote a post about security and backdoors, prompted by both the FBI/Apple controversy and by Kim Zetter’s talk at M3AAWG about Stuxnet. These questions about control and access will only get more complicated as we produce, consume, store, and share more data across more devices.
Speaking of predictions, I also noted my contribution to a great whitepaper from Litmus that explores the state of Email Marketing in 2020.
As always, we looked at some best practices this month. I wrote up some of my thoughts about data hygiene following Mailchimp’s blog post about the value of inactive subscribers. As always, there isn’t one right answer, but there’s a lot of good food for thought. And more food for thought: how best practices are a lot like public health recommendations. As with everything, it comes down to knowing your audience(s) and looking at the relationship(s), which, as you know, is a favorite subject around here.

Laura's Speaking Events early 2016
Fraud, terms of service and email marketing

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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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April 2015: The Month in Email

We started the month with some conversations about best practices, both generally looking at the sort of best practices people follow (or don’t) as well as some specific practices we wanted to look at in more depth. Three for this month:

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September 2014: The Month in Email

September was another busy month for us, but Steve stepped up and wrote a number of really interesting posts on email history, cryptography, and current technical issues in the email landscape.
We started the month with a look at the various RFCs that served as the technical specifications for developing message transfer protocols in the 1970s. It’s really fascinating to look at the evolution of these tools we use every day 40 years later. We followed up with a second post on the origins of network email, which is a great primer (or refresher) on the early days of email.
Steve’s four-part series on cryptography and email started with an in-depth look at how the industry is evolving with respect to encryption and privacy issues. He then introduced us to Alice and Bob (or reintroduced those of us who have been following the adventures of the first couple of cryptography), and described symmetric-key and public-key encryption. His next post described message signing, and how DKIM is used to manage this. He finished up the series with a post on PGP keys.
In industry news: Spamcop is shutting down its email service. There shouldn’t be any major impact on senders, but the post has some specific notes on DMARC implications. We also noted an interesting mail routing suggestion on Twitter, and wrote a post on using Mail.app for this.
In other DMARC news, we wrote about DMARC and report size limits, which might be useful information, depending on your configuration. We also launched a new DMARC tool to help senders understand who is publishing DMARC. Let us know what you think and if you’re finding it useful.
We couldn’t let a month go by without mentioning filters. We looked at a sector we don’t usually discuss, corporate filtering, and went in-depth on a much-misunderstood topic, content filtering.
Finally, Laura offered a webinar on a favorite topic, deliverability, in conjunction with the AMA and Message Systems. If you missed it, you can watch the recorded version here, or just take a peek at some of the reaction via Twitter.

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