It's not a technical problem

You can’t technical your way out of the bulk folder. I wrote that a year and a half ago, and it’s even more true today. Filters at the big webmail providers continue to evolve to meet new threats and new spamming techniques. Sending technically perfect mail won’t get your mail into the inbox. Recipients have to want the mail and interact with the mail for good delivery.
 

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It depends… no more

The two most hated words in deliverability. Many people ask general questions about deliverability and most experts, including myself, answer, “It depends.”
There are a lot of problems with this answer. The biggest problem is that it’s led to the impression that there are no real answers about deliverability. That because we can’t answer hypothetical questions we are really just making the answers up.
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The reason we use “it depends” is because the minute details matter when it comes to deliverability. Wether or not something will hurt or help deliverability depends on the specific implementation. Who’s doing the sending? What is their authentication setup? What IP are they using? How were the addresses collected? What is their frequency? What MTA is used? Are they linking to outside sites? Are they linking to outside services? Where are images hosted? The relevant questions go on and on and on.
I am going to stop saying it depends when answering generic deliverability questions. Instead I will be using the phrase “details matter.” Details do matter. Details are everything. Details drive deliverability.
Details Matter
The importance of details is why many deliverability people hedge their answers. The details do matter.
I will do my best to stop answering It Depends to deliverability questions. Instead, I’ll be answering with question and pointing out the details matter.
 

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Permission and B2B spam

Two of the very first posts I wrote on the blog were about permission (part 1, part 2). Re-reading those posts is interesting. Experience has taught me that recipients are much more forgiving of implicit opt-in than that post implies.
The chance in recipient expectations doesn’t mean, however, that permission isn’t important or required. In fact, The Verge reported on a chatbot that will waste the time of spammers. Users who are fed up with spam can forward their message to Re:Scam and bots will answer the mail.
I cannot tell you how tempted I am to forward all those “Hey, just give me 10 minutes of your time…” emails I get from B2B spammers. I know, those are actually bots, but there is lovely symmetry in bots bothering one another and leaving us humans out of it.

Speaking of those annoying emails, I tweeted about one (with horrible English…) last week. I tagged the company in question and they asked for an example. After I sent it, they did nothing, and I continued to get mail. Because of course I did.
These types of messages are exactly why permission is so critical for controlling spam. Way more companies can buy my email address and add me to their spam automation software than I can opt-out of in any reasonable time frame. My inbox, particularly my business inbox, is where I do business. It’s where I talk with clients, potential clients, customers and, yes, even vendors. But every unsolicited email wastes my time.
It’s not even that the mail is simply unwanted. I get mail I don’t want regularly. Collecting white papers for my library, RSVPing to events, joining webinars all result in me getting added to companies’ mailing lists. That’s fair, I gave them an email address I’ll unsubscribe.
The B2B companies who buy my address are different. They’re spamming and they understand that. The vendors who sell the automation filters tell their customers how to avoid spam filters. Spammers are told to use different domains for the unsolicited mail and their opt-in mail to avoid blocking. The software plugs into Google and G Suite account because very few companies will block Google IPs.
I’ve had many of these companies attempt to pay me to fix their delivery problems. But, in this case there’s nothing to fix. Yes, your mail is being blocked. No, I can’t help. There is nothing I can say to a filtering company or ISP or company to make them list that block. The mail is unwanted and it’s unsolicited.
The way to get mail unblocked is to demonstrate the mail is wanted. If you can’t do that, well, the filters are working as intended.
 

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Filters do what we tell them

In the email space we talk about filters as if they were sentient beings. “The filters decided…” “The filters said…” This is convenient shorthand, but tends to mask that filters aren’t actually deciding or saying anything. Filters are software processes that follow rules dictated by the people who create and maintain them. The rules flow from the goals set by the mailbox provider. The mailbox provider sets goals based on what their users tell them. Users communicate what they want by how they interact with email.

What we end up with is a model where a set of people make decisions about what mail should be let in. They pass that decision on to the people who write the filters. The people who write the filters create software that evaluates email based on those goals using information collected from many places, including the endusers.
What mail should be let in is an interesting question, with answers that differ depending on the environment the filter is deployed in.
Consumer ISPs typically want to keep their users happy and safe. Their goals are to stop harmful mail like phishing, or mail containing viruses or malware. They also want to deliver mail that makes their users happy. As one ISP employee put it, “We want our users to be delighted with your mail.”
Businesses have a few other goals when it comes to filters. They, too, need filters to protect their network from malicious actors. As businesses are often directly targeted by bad actors, this is even more important. They also want to get business related email, whether that be from customers or vendors. They may want to ensure that certain records are kept and laws are followed.
Governments have another set of goals. Universities and schools have yet another set of goals. And, of course, there are folks who run their own systems for their own use.
Complicating the whole thing is that some groups have different tolerances for mistakes. For instance, many of our customers are folks dealing with being blocked by commercial filters. Therefore, we don’t run commercial filters. That does mean we see a lot of viruses and malware and rely on other strategies to stop a compromise, strategies that wouldn’t be as viable in a different environment.
Filters are built to meet specific user needs. What they do isn’t random, it’s not unknowable. They are designed to accomplished certain goals and generally they’re pretty good at what they do. Understanding the underlying goals of filters can help drive solutions to poor delivery.
Use the shorthand, talk about what filters are doing. But remember that there are people behind the filters. Those filters are constantly maintained in order to keep up with ever changing mail streams. They aren’t static and they aren’t forgotten. They are updated regularly. They are fluid, just like the mail they act on.

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