You can't technical yourself out of delivery problems

In many cases these days, many more cases than a lot of senders want to admit, delivery problems at the big ISPs are a result of sending mail recipients just don’t care about. The reason your mail is going to bulk? It’s not because you have minor problems in your headers. It’s not because you have some formatting issues. The reason is because your recipients just don’t care if the ISP delivers your mail or not.
A few years ago the bulk of my clients hired me to do technical audits for their mail. I fixed a lot of delivery problems that way. They’d send me their email and I’d run it through tools here and identify things they were doing that were likely to be causing problems. I’d give them some suggestions of things to change. Believe it or not, minor tweaks to headers and configuration actually did make a lot of difference in delivery.
Over time, though those tweaks less effective to fix delivery problems. Some of it is due to the MTA vendors, they’re a lot better at sending technically correct mail than they were before. There are also a lot more people giving good advice on the underlying structure and format of emails so senders can send technically clean email. I started seeing technically perfect emails from clients who were seeing major delivery problems.
There are a number of reasons that technical fixes don’t work like they used to. The short version, though, is that ISPs have dealt with much of the really blatant spam and they can focus more time and energy on the “grey mail”.
This makes my job a little harder. I can no longer just look at an email, maybe run it through some of our tools and provide a few suggestions that fix delivery problems. Delivery isn’t that simple any longer. Filters are really more focused on how the recipients react to mail. That means I need to know a lot more about a clients email program before I can even start to identify what might be causing the delivery issues.
I wish it were still so simple I could give minor technical tweaks that would appear to magically improve a client’s delivery. It was a lot simpler process then. But filters have evolved, and senders must evolve, too.

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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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More than just getting past the filters

I’ve been feeling a little philosophical lately. My thoughts are meandering a lot around the whys and the deeper issues surrounding stuff, including email. It means I’m a bit more distracted and less focused than usual. And more prone to pose questions than usual. This was part of the introspection that led me to write the motivating people post last week. I’m trying to figure out how to motivate volunteers in two different realms. And there’s always the question of how do I present a solution to clients in a way that motivates them to take my advice. Sure, I get paid either way, but I really like it when clients take my advice and see success.
There are other places this mental meandering is taking me.
I’m currently working on a project for a client. This particular client is struggling to get mail delivered to a very mobile business audience. In the target field, people change jobs regularly and email addresses can change multiple times a year. One of the things I’m working on for them is how to get email to the right people, that is the people who opted in, when their addresses change so frequently.
This is delivery consulting, but this project really brings home how much more there is to delivery than avoiding filters. Filters are the least of this client’s problem. The real problem is the mobility of their audience. As I was thinking about how to address this issue of mobility, I realized that my job as a delivery expert has gone well beyond telling people how to get their mail past filters.
My job is much more about helping people succeed at what it is that they’re trying to do with email. How can email work for you and for your target audience?
Looking at the broader picture means I’m less likely to focus on the minutia of “spam words” and subject lines and best time of day to send. Sure, there are always tweaks to make in an email. There are always things to test. There are always changes to try. But the effect of those changes is not near as great as actually sending mail that meets the needs of the audience.
Often clients come to me so overwhelmed in the details they forget the bigger picture. I help them find that picture again. My job is much more than getting through the filters, it’s about finding success for clients.

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Filters and windmills

A colleague of mine was dealing with a client who is experiencing some difficulty delivering to the bulk folder. Said client spent much of a one hour phone call repeating “This is not how a free society works!!”
After the call my colleague commented, “I refuse to get ranty about filter systems.”
I know that filters, and the people who write and maintain them, are a frequent scapegoat for senders. The filters are always the problem, not anything the senders do.
Now, I’ll be the last person who will claim spam filters are perfect, they’re not. Filters sometimes do unexpected things, sometimes they do boneheaded things, sometimes they are broken.
We can’t forget, though, that filters perform a vital role in protecting users from malicious emails. Phishing emails, scams, fake products, viruses are a constant threat. Many end users don’t need to worry about this because filters are so good. But an unfiltered account can get thousands of scams and spams a day (ask me how I know).
Most of us in the delivery space can tell when a filter is working as intended and when there’s an underlying problem. And when the filter is working as intended there’s not a lot of use complaining about them. Ranting about filtering systems often delays a resolution. Senders that focus on what they can control tend to have more success reaching the inbox than those senders that focus on ranting about filtering systems.
Tilting at windmills doesn’t get the mail through.

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