Filters evolving

I started writing this blog post while sitting on a conference call with a bunch of senders discussing some industry wide problems folks are having with delivery. Of course the issue of Microsoft comes up. A lot of senders are struggling with reaching the inbox there and no one has any real, clear guidance on how to resolve it. And the MS employees who regularly answer questions and help folks have been quiet during this time.

In some ways the current situation with Microsoft reminds me of what most deliverability was like a decade ago. Receivers were consistently making changes and they weren’t interacting with senders. There weren’t FBLs really. There weren’t postmaster pages. The reason knowing someone at an ISP was so important was because there was no other way to get information about blocking.
These days, we have a lot more institutional knowledge in the industry. The ISPs realized it was better to invest in infrastructure so senders could resolve issues without having to know the right person. Thus we ended up with postmaster pages and a proliferation of FBLs and best practices and collaboration between senders and receivers and the whole industry benefited.
It is challenging to attempt to troubleshoot deliverability without the benefit of having a contact inside ISPs. But it is absolutely possible. Many ISP folks have moved on over the years; in many cases due to layoffs or having their positions eliminated. The result is ISPs where there often isn’t anyone to talk to about filters.
The lack of contacts doesn’t mean there’s no one there and working. For instance, in the conference call one person asked if we thought Microsoft was going to fix their systems or if this is the new normal. I think both things are actually true. I think Microsoft is discovering all sorts of interesting things about their mail system code now that it’s under full load. I think they’re addressing issues as they come up and as fast as they can. I also think this is some level of a new normal. These are modern filters that implement the lessons learned over the past 20 years of spam filtering without the corresponding cruft.
Overall, I do think we’re in a period of accelerating filter evolution. Address filtering problems has always been a moving target, but we’ve usually been building on known information. Now, we’re kinda starting over. I don’t have a crystal ball and I don’t know exactly what the future will bring. But I think the world of deliverability is going to get challenging again.
 

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The delivery communication gap

There seems to be a general uptick in the number of specific questions that ESPs and commercial senders are asking recently. I’m getting them from clients, and I’m hearing similar stories from my various contacts over on the ISP side. The questions cover a wide range of areas in email delivery, but the underlying issue is really that there are no real fixed rules about email delivery anymore. The only rule is “send mail users want to receive” and there are no specific guidelines to how to do that.
This is frustrating for a lot of people. They want to know exactly how many complaints they need to stay under. They want to know what “engagement” means and how exactly the ISPs are measuring it. They want to know all of the metrics they need to meet in order to get mail to the inbox.
There is a lot of frustration among senders because they’re not getting the answers they think they need and they feel like the ISPs aren’t listening to them.
Likewise there is a lot of frustration among ISPs because they’re giving answers but they feel like they’re not being heard.
Some of the problem is truly a language difference. A lot of delivery people on the ESP side are marketers first and technologists second. They don’t have operational experience. They don’t have that any feel for the technology behind email and can’t map different failure modes onto their causes. Some of them don’t have any idea how email works under the covers. Likewise, a lot of postmaster people are technologists. They deeply understand their customers and their email servers and don’t speak marketing.
The other issue is the necessary secrecy. Postmasters have been burned in the past and so they have to be vague about what variables they are measuring and how they are weighting them.
All of this leads to a very adversarial environment.
I’ve been talking with a lot of people about this and none of us have any real answers to the solution. Senders say the ISPs should spend more time explaining to the senders what they need to do. ISPs say the senders should stop sending spam.
Am I quite off base here? Is there no communication gap? Am I just cynical and missing some obvious solution? Anyone have any suggestions on how to solve the issue?

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Getting whitelisted by endusers

One of the best ways to ensure mail is delivered to a recipients inbox is to encourage the recipient to add the senders from: address to their address book. In cases where an ISP might otherwise bulk folder the email, they will instead put the email into the inbox.
Senders are changing their practices to get recipients to add from addresses to address books. There are a number of companies reminding users to add addresses on the webpage at the time of signup. Most emails have recommendations in each email. Recently, there have been multiple reports of companies who send specific email campaigns to encourage recipients to whitelist the sender.
Cool Email Idea: Customized Whitelisting Instructions from ReturnPath.
How & Why You Need to be Added to Your Recipient’s Address Book from VerticalResponse.
In addition to the direct benefit to the recipient that whitelists the individual sender, there are some hints that ISPs are looking at individual whitelisting as part of their internal sender reputation scoring.

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Email and law in the news

A couple things related to the intersection of email and law happened recently.
The 6th circuit court ruled that the government must have a search warrant before accessing email. The published opinion is interesting reading, not just because of the courts ruling on the law but also because of the defendant. Berkeley Premium Nutraceuticals toyed with spamming to advertise their product as a brief search of public reporting sites shows. The extent and effort they went to in order to stay below the thresholds for losing their merchant accounts is reminiscent of the effort some mailers go through to get mail through ISP filters.
The other bit of interesting reading is the Microsoft motion to dismiss the case brought against them by Holomaxx. It is a relatively short brief (33 pages) and 3 of those pages are simply a listing of the relevant cases demonstrating ISPs are allowed to filter mail as they see fit. 2 more pages are dedicated to listing the relevant Federal and State statutes. I strongly encourage anyone considering suing any large ISP to to read this pleading. These lawyers understand email law inside and out and they are not going to mess around. They also have both statute and case law on their side. They point this out before the end of page 1:

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