Thinking about deliverability

I was chatting with folks over on one of the email slack channels today. The discussion was about an ESP not wanting to implement a particular change as it would hurt deliverability. It led me down a path of thinking about how we think of deliverability and how that informs how we approach email.
The biggest problem I see is the black and white thinking.
There’s an underlying belief in the deliverability, receiving, and filtering communities  that the only way to affect sending behavior is to block (or threaten to block) mail.

This was true back in the ancient times (the late 90’s). We didn’t have sophisticated tools and fast CPUs. There weren’t a lot of ways to handle bad mail other than to block. Now the landscape is different. We have many more tools and the computing capacity to quickly sort large streams of data.
At most places these days, blocking is an escalation, not a warning shot. Many places rate limit and bulk folder questionable mail as a first strike against problem mail. Sometimes the mail is bad enough to result in a block. Other times, it’s not bad enough to block, so it disappears into the bulk folder.
There’s a corresponding belief in the sending community that if their behavior doesn’t result in blocking then they’re acting acceptably. This isn’t true either. There are a lot of things you can do (or not do) that don’t help delivery, but will actively harm delivery. Likewise, there are things you can do that don’t actively harm delivery, but will help. All of these things add up to reaching the inbox.

It’s all shades of grey

Things don’t happen on a short timeline. Bad email behavior might take days, weeks or even months to affect things.
Take the situation where a company buys a list and starts sending spam. On one side we have anti-spammers on the other we have marketers.
Anti-spammers often react to the spam to a purchased list with bluster and threats. This behavior is illegal! It’s against CAN SPAM! All your mail will be blocked! Your ESP will throw you off! Yeah, no. That’s not how it works back here in the real world. Purchasing lists is not illegal under CAN SPAM. Blocking might happen, but unless it’s a filthy list it’s not likely to happen the first time. Many ESPs will work with senders, requiring them to remove the purchased list but allowing them to continue mailing their regular lists. Eventually, people start ignoring the boy who cried spam.
It’s not like senders are all honest about the effects of purchased lists, either. Talk to a few marketers and they will swear blind purchased lists are great. They’re kinda right, in the short term under very specific conditions. If the sender starts out with a good reputation, makes smart purchases, and pays attention they’ll often get away with purchasing lists for a while. Eventually, though, delivery problems show up. But because the problems take so long to show up, they refuse to believe purchasing lists led to their mail going to bulk.
In both cases we have folks who aren’t looking at the whole picture. Thus, you end up with delivery folks who simplify their message to “it will hurt deliverability” when the reality is a lot more complex. Sometimes senders have a bad ideas that shouldn’t be done, even though they won’t hurt deliverability. But they won’t listen to any advice containing more realistic consequences.
 
 

About those degrees…
Microsoft changes

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It's not fair

In the delivery space, stuff comes in cycles. We’re currently in a cycle where people are unhappy with spam filters. There are two reasons they’re unhappy: false positives and false negatives.
False positives are emails that the user doesn’t think is spam but goes into the bulk folder anyway.
Fales negatives are emails that the user does thing is spam but is delivered to the inbox.
I’ve sat on multiple calls over the course of my career, with clients and potential clients, where the question I cannot answer comes up. “Why do I still get spam?”
I have a lot of thoughts about this question and what it means for a discussion, how it should be answered and what the next steps are. But it’s important to understand that I, and most of my deliverability colleagues, hate this question. Yet we get it all the time. ISPs get it, too.
A big part of the answer is because spammers spend inordinate amounts of time and money trying to figure out how to break filters. In fact, back in 2006 the FTC fined a company almost a million dollars for using deceptive techniques to try and get into filters. One of the things this company did would be to have folks manually create emails to test filters. Once they found a piece of text that would get into the inbox, they’d spam until the filters caught up. Then, they’d start testing content again to see what would get past the filters. Repeat.
This wasn’t some fly by night company. They had beautiful offices in San Francisco with conference rooms overlooking Treasure Island. They were profitable. They were spammers. Of course, not long after the FTC fined them, they filed bankruptcy and disappeared.
Other spammers create and cultivate vast networks of IP addresses and domains to be used in snowshoeing operations. Still other spammers create criminal acts to hijack reputation of legitimate senders to make it to the inbox.
Why do you still get spam? That’s a bit like asking why people speed or run red lights. You still get spam because spammers invest a lot of money and time into sending you spam. They’re OK with only a small percentage of emails getting through filters, they’ll just make it up in volume.
Spam still exists because spammers still exist.
 

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5 Simple Tricks to Reach the Inbox

I saw a post over on LinkedIn today. It was from an ESP, talking about their simple tips and tricks for getting into the inbox. The laughable bit was half the “tricks” had nothing to do with getting to the inbox, but rather were about enticing people to open the mail once it’s gotten to the inbox.
There are no “tricks” to getting to the inbox. There used to be some tricks. But the ISPs figured them out and protect against them.

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August 2017: The month in email

Hello! Hope all are keeping safe through Harvey, Irma, Katia and the aftermath. I know many people that have been affected and are currently out of their homes. I am proud to see so many of my fellow deliverability folks are helping our displaced colleagues with resources, places to stay and money to replace damaged property.
Here’s a mid-month late wrapup of our August blog posts. Our favorite part of August? The total eclipse, which was absolutely amazing. Let me show you some pictures.





Ok, back to email.
We’re proud of the enormous milestone we marked this month: ten years of near-daily posts to our Word to the Wise blog. Thanks for all of your attention and feedback over the past decade!
In other industry news, I pointed to some interesting findings from the Litmus report on the State of Email Deliverability, which is always a terrific resource.
I also wrote about the evolution of filters at web-based email providers, and noted that Gmail’s different approach may well be because it entered the market later than other providers.
In spam, spoofing, and other abuse-related news, I posted about how easy it is for someone to spoof a sender’s identity, even without any technical hacks. This recent incident with several members of the US presidential administration should remind us all to be more careful with making sure we pay attention to where messages come from. How else can you tell that someone might not be wholly legitimate and above-board? I talked about some of what I look at when I get a call from a prospective customer as well as some of the delightful conversations I’ve had with spammers over the years.
In the security arena, Steve noted the ongoing shift to TLS and Google’s announcement that they will label text and email form fields on pages without TLS as “NOT SECURE”. What is TLS, you ask? Steve answers all your questions in a comprehensive post about Transport Layer Security and Certificate Authority Authorization records.
Also worth reading, and not just for the picture of Paddington Bear: Steve’s extremely detailed post about local-part semantics, the chunk of information before the at sign in an email address. How do you choose your email addresses (assuming they are not assigned to you at work or school…)? An email address is an identity, both culturally and for security purposes.
In subscription best practices — or the lack thereof — Steve talked about what happens when someone doesn’t quite complete a user registration. Should you send them a reminder to finish their registration? Of course! Should you keep sending those reminders for 16 months after they’ve stopped engaging with you? THE SURPRISING ANSWER! (Ok, you know us. It wasn’t that surprising.)

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