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.

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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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Setting expectations at the point of sale

In my consulting, I emphasize that senders must set recipient expectations correctly. Receiver sites spend a lot of time listening to their users and design filters to let wanted and expected mail through. Senders that treat recipients as partners in their success usually have much better email delivery than those senders that treat recipients as targets or marks.
Over the years I’ve heard just about every excuse as to why a particular client can’t set expectations well. One of the most common is that no one does it. My experience this weekend at a PetSmart indicates otherwise.
As I was checking out I showed my loyalty card to the cashier. He ran it through the machine and then started talking about the program.
Cashier: Did you give us your email address when you signed up for the program?
Me: I’m not sure, probably not. I get a lot of email already.
Cashier: Well, if you do give us an email address associated with the card every purchase will trigger coupons sent to your email address. These aren’t random, they’re based on your purchase. So if you purchase cat stuff we won’t send you coupons for horse supplies.
I have to admit, I was impressed. PetSmart has email address processes that I recommend to clients on a regular basis. No, they’re not a client so I can’t directly take credit. But whoever runs their email program knows recipients are an important part of email delivery. They’re investing time and training into making sure their floor staff communicate what the email address will be used for, what the emails will offer and how often they’ll arrive.
It’s certainly possible PetSmart has the occasional email delivery problem despite this, but I expect they’re as close to 100% inbox delivery as anyone else out there.

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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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