The perfect email

More and more I’m moving away from consulting on technical setup issues as the solution to delivery problems. Delivery is not about the technical perfection of a message. Spammers get the technical right all the time. No, instead, delivery is about sending messages the user wants. While looking for something on the blog I found an old post from 2011 that’s still relevant today. In fact, I’d say it’s even more relevant today than it was when I wrote it 5 years ago.
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Email is a fluid and ever changing landscape of things to do and not do.
Over the years my clients have frequently asked me to look at their technical setup and make sure that how they send mail complies with best practices. Previously, this was a good way to improve delivery. Spamware was pretty sloppy and blocking for somewhat minor technical problems was a great way to block a lot of spam.
More recently filter maintainers have been able to look at more than simple technical issues. They can identify how a recipient interacts with the mail. They can look at broad patterns, including scanning the webpages an email links to.
In short, email filters are very sophisticated and really do measure “wanted” versus “unwanted” down to the individual subscriber levels.
I will happily do technology audits for clients. But getting the technology right isn’t sufficient to get good delivery. What you really need to consider is: am I sending email that the recipient wants? You can absolutely get away with sloppy technology and have great inbox delivery as long as you are actually sending mail your recipients want to receive.
The perfect email is no longer measured in how perfectly correct the technology is. The perfect email is now measured by how perfect it is for the recipient.

Ask Laura: Should I let my ESP give me a shared IP?
Microsoft deprecating SmartScreen filters

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Emails that make you smile

This summer’s non-work project for me has been training for a 5K run with Fleet Feet in Menlo Park. As part of the training programs we get weekly emails from the store on Monday. As I was reading through today’s email, I found myself smiling and happy. Lisa, who is one of the store owners and writes the emails, is just so happy and bouncy and thrilled to share her love of running and that comes through in the newsletter.
Our group’s primary coach is the other store owner. During runs we often talk about random stuff, and when I tell people I do email delivery, they always start talking about their experience with email and spam. One night I was running with Jim, and we were talking about Jim’s experiences with sending email. He mentioned their ESP and talked about how convenient it was. But then he mentioned he wasn’t sure that they were sending enough mail (which made me laugh hard enough I almost tripped on a curb).
I realized I am not just a delivery expert when I started thinking about all the ways they could increase the amount of email they send, while still maintaining the quality and the friendly feel of their bulk emails. What could they offer local runners that would increase the value of the store to them? The first very obvious thing was a race calendar. There are dozens of local races every week, telling folks about upcoming races and entry deadlines would be a way to contact folks regularly without it always being a “buy stuff from us!!”
What commercial emails have you gotten recently that have made you smile?

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The Physics of the Email Universe

We talk a lot about rules and best practices in email, but we’re mostly talking about “squishy” rules-of-thumb that are based on simplified models of how mail systems, spam filters, recipients, postmasters and blacklist operators behave. They’re the biology, ecology and sociology of the email ecosystem.
There’s another set of rules we tend to only mention in passing, if at all, though. They’re the steely, sharp-edged laws that control the email universe. They’re the RFCs that define how email works and make sure that mail systems written by hundreds of different people across the globe all work and all interoperate with each other.
Building a message from Zeros and Ones
RFC 5322 – Internet Message Format
This tells you everything you need to know about crafting a simple email, with a subject line, a sender, some recipients and a simple plain-text message. It’s also the foundation of all fancier emails. If you’re creating emails, this is where to start.
A little more than plain ASCII
RFC 2047 – MIME Part 3: Message Header Extensions for Non-ASCII Text
RFC 2047 is one small part of the MIME (Multipurpose Internet Mail Extensions) suite of protocols that allow you to include pictures and attachments and prettily formatted text and comic sans in your email. This part defines how you can put things other than the plainest of plain text in your subject lines or in the “friendly from” of your message. It’s what allows you to put Hiragana, or Cyrillic, or umlauts, or cedillas, or properly matched double quotes in your subject line. It also let’s you put hearts or smiley faces or other little pictograms there – but nothing this useful is going to be perfect.
RFC 2045 – MIME Part 1: Format of Internet Message Bodies
This shows how to send an image, or a plain text mail in a different character set, or an HTML mail. It doesn’t tell you how to send plain text and HTML, or to send HTML with embedded images, or a message with an attached document. For that you need…
Finally, Modern Email
RFC 2046 – MIME Part 2: Media Types
This builds on RFC 2045 to allow you to have many different chunks in a message – this is what you need if you want to send “proper” HTML mail with a plain text alternative, or if you want embedded images or attachments.
Getting From A To B
RFC 5321 – Simple Mail Transfer Protocol
A message isn’t much use unless you send it somewhere. RFC 5321 explains the mysteries of actually sending that message over the wire to the recipient. If you need to know about the different phases of a message delivery, what “4xx” and “5xx” actually mean, why there’s not really any such thing as a hard or soft bounce defined, just temporary or permanent failures, or anything else about actually sending mail or diagnosing mail delivery, this is your starting point.
The Rest Of The Iceberg
I’ve only touched on the very smallest tip of the email iceberg here. There’s much, much more – both in RFCs and ad-hoc non-RFC standards. If you’re interested in more, this is a decent place to start.

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Check your tech

One of the things we do for just about every new client coming into WttW is have them send us an email from their bulk mail system. We then check it for technical correctness. This includes things like reviewing all the different From headers, rDNS of the connecting IP, List-Unsubscribe headers and authentication. This is always useful, IMO, because we often find things that were right when they were set up, but due to other changes at the customer they’re not 100% correct any more.
This happens to most of us. Even a company as small as Word to the Wise misses a rDNS update here or a hostname change update there when making infrastructure changes. That’s even when the same people know about email and are responsible for the infrastructure.
One of the most common problems we see is a SPF record that has accumulated include: files from previous providers. There are a couple reasons for this. One is the fact that SPF is set up while still at the old provider in anticipation of moving to the new provider. Once the move is made no one goes back to clean up the SPF record and remove the old entries. The other reason is that a lot of tech folks don’t like to delete things. Deleting things can lead to problems, and there’s no harm in a little extra in the SPF record. Except, eventually, there are so many include files that the lookup fails.
Every mailer should schedule a regular tech audit for their mail. Things change and sometimes in the midst of chance we don’t always catch some of the little details.

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