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.

5 Years
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Last time I worked with the actual HTML design of emails (a long time ago), <head> was not really needed. Is this still true for the most part? Any reason why you still want to include <head> + meta, title tags in emails nowadays?

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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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Why do ISPs do that?

One of the most common things I hear is “but why does the ISP do it that way?” The generic answer for that question is: because it works for them and meets their needs. Anyone designing a mail system has to implement some sort of spam filtering and will have to accept the potential for lost mail. Even the those recipients who runs no software filtering may lose mail. Their spamfilter is the delete key and sometimes they’ll delete a real mail.
Every mailserver admin, whether managing a MTA for a corporation, an ISP or themselves inevitably looks at the question of false positives and false negatives. Some are more sensitive to false negatives and would rather block real mail than have to wade through a mailbox full of spam. Others are more sensitive to false positives and would rather deal with unfiltered spam than risk losing mail.
At the ISPs, many of these decisions aren’t made by one person, but the decisions are driven by the business philosophy, requirements and technology. The different consumer ISPs have different philosophies and these show in their spamfiltering.
Gmail, for instance, has a lot of faith in their ability to sort, classify and rank text. This is, after all, what Google does. Therefore, they accept most of the email delivered to Gmail users and then sort after the fact. This fits their technology, their available resources and their business philosophy. They leave as much filtering at the enduser level as they can.
Yahoo, on the other hand, chooses to filter mail at the MTA. While their spamfoldering algorithms are good, they don’t want to waste CPU and filtering effort on mail that they think may be spam. So, they choose to block heavily at the edge, going so far as to rate limit senders that they don’t know about the mail. Endusers are protected from malicious mail and senders have the ability to retry mail until it is accepted.
The same types of entries could be written about Hotmail or AOL. They could even be written about the various spam filter vendors and blocklists. Every company has their own way of doing things and their way reflects their underlying business philosophy.

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