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Deliverability strategy to reach the inbox

I wrote a piece for the Only Influencers special Holiday Preparations edition about deliverability and the holiday email rush. One thing I like about the chance to write for other publications is the process often leads me down thought pathways and generate some new ideas.

Still Spamming…

This morning I woke up to news that Sanford Wallace pled guilty to spamming. Again.
Sanford was one of the very early spammers (savetrees.com). He moved to email from junk faxing when Congress made junk faxing illegal in 2005. He sued AOL when AOL blocked his mail. He lost and the courts maintained that blocking spam was not a violation of the sender’s rights. Sanford then moved on to using open relays to avoid blocks. He was eventually disconnected from his backbone provider (AGIS) for abuse. Sanford sued AGIS for breach of contract and was reconnected for a brief period of time.
After his disconnection from AGIS, Sanford and a few of the other folks proposed a backbone provider that allowed bulk email marketing. That never really went anywhere.
Reading these old articles is a major blast in the past. The legal case between AGIS and Cyberpromotions was the event that led to my involvement in email marketing and spam. I even spent a Saturday afternoon in the late 90s with about a dozen people on a con call with Sanford and Walt talking about his backbone idea. My position was pretty simple: it wasn’t going to work, but as long as there was consent it was his network and he could do what he wanted.
I kinda lost track, just because he moved onto other ways of advertising and I got deeper and deeper into deliverability consulting. He did show up on my radar a few years ago when Facebook sued him for breaking into user accounts and using those accounts to spam. He lost a $711 million dollar judgement to Facebook, but given he didn’t have the resources the judge in that case recommended criminal charges.
Criminal charges were filed a few years later. Yesterday, Sanford pled guilty to fraud and criminal contempt as well as violating a court order to stay off Facebook’s network.
He now faces $250,000 in fines and up to 16 years in jail. Given his history, I expect he’ll figure out some way to still send spam even if he’s locked up.
Sanford is one of the reasons so many folks have such a low opinion of anyone who describes their business as “legitimate email marketing.” Sanford used the same phrase back in the late 90s. Of course no one, with the possible exception of him, actually believed that. But when someone like that adopts the moniker “legitimate email marketer” it’s hard to take them seriously when someone like Sanford has been using that since the late 90s.

Check your tech

One of the things we do for just about every new client coming into WttW is have them send us an email from their bulk mail system. We then check it for technical correctness. This includes things like reviewing all the different From headers, rDNS of the connecting IP, List-Unsubscribe headers and authentication. This is always useful, IMO, because we often find things that were right when they were set up, but due to other changes at the customer they’re not 100% correct any more.
This happens to most of us. Even a company as small as Word to the Wise misses a rDNS update here or a hostname change update there when making infrastructure changes. That’s even when the same people know about email and are responsible for the infrastructure.
One of the most common problems we see is a SPF record that has accumulated include: files from previous providers. There are a couple reasons for this. One is the fact that SPF is set up while still at the old provider in anticipation of moving to the new provider. Once the move is made no one goes back to clean up the SPF record and remove the old entries. The other reason is that a lot of tech folks don’t like to delete things. Deleting things can lead to problems, and there’s no harm in a little extra in the SPF record. Except, eventually, there are so many include files that the lookup fails.
Every mailer should schedule a regular tech audit for their mail. Things change and sometimes in the midst of chance we don’t always catch some of the little details.

Utilizing all of your data

Email marketing continues to be a great way to reach out to prospects and customers and many companies utilize multiple mail streams. Companies often have the following systems sending mail:

The FTC answers questions about CAN SPAM

The FTC posted answers to a number of questions about the CAN SPAM act.

Linking identities to email addresses

As I predicted yesterday, a bunch of sites have popped up where you can input email addresses and find out if the address was part of the Ashley Madison hack. My spam trap address isn’t on it, which makes me wonder if unsubscribe data was kept elsewhere or if they just never bothered to save the requests.
One of the things I’m seeing in most articles about the hack is reassurance that Ashley Madison doesn’t verify addresses, so the accounts may not belong to the email address in question. We can’t say that the email address owner is the cheater, because Ashley Madison didn’t care who owned the email address.
The warnings have been published in security blogs.

Ashley Madison Compromise

Last month Brian Krebs reported that the Ashley Madison database was compromised. Ashley Madison is a dating site that targets married folks who are looking to have affairs. Needless to say, there is a lot of risk for users if their data is found on the released data. Today what is supposedly the Ashley Madison data was released.
The release of this data can have some significant impacts on the site members. Of course there’s the problem of credit card numbers being stolen, but that’s something most of us have to deal with on a regular basis. But there can also be significant relationship repercussions if/when a spouse discovers that their partner has registered on a site to have affairs.
When I first heard of the compromise I wondered if they had my data. You see, they have one of my spamtraps on their unsubscribe list. It just so happened that I visited an unsubscribe link, hosted by Ashley Madison (http://unsub.ashleymadison.com/?ref=2). This was during the time when I decided to unsubscribe from all the spam coming into one of my spamtraps. Is my email address going to be a part of this data dump? If my email address is there, what name do they have associated with it? This is the trap that gets mail addressed to multiple other people. Maybe it’s my email address but their name. Are they at risk for relationship problems or legal problems due to my attempt to unsubscribe?
Of course, Ashley Madison had no incentive to make sure their data was correct. In fact, they were sued for faking data to entice paying members. How much of the released data is false and will there be real harm due to that?
I expect in the next few days someone (or multiple someones) will put up a website where those of us who are curious can search the data. I just hope that people realize how much of the data is likely to be false. Even Arstechnica cautions readers from jumping to conclusions.

TXTing

txt
On Friday I talked a bit about the history behind TXT records, their uses and abuses.
But what’s in a TXT record? How is it used? When and where should you use them?
Here’s what you get if you query for the TXT records for exacttarget.com from a unix or OS X command line with dig exacttarget.com txt

A brief history of TXT Records

txt
When the Domain Name System was designed thirty years ago the concept behind it was pretty simple. It’s mostly just a distributed database that lets you map hostname / query-type pairs to values.
If you want to know the IP address of cnn.com, you look up {cnn.com, A} and get back a couple of IP addresses. If you want to know where to send mail for aol.com users, you look up {aol.com, MX} and you get a set of four hostname / preference pairs back. If you want to know the hostname for the IP address 206.190.36.45 you look up {45.36.190.206.in-addr.arpa, PTR} and get a hostname back.
There’s a well-defined meaning to each of those query types – A is for IP addresses, MX is for mailservers, PTR is for hostnames – and that was always the intent for how DNS should work.
When DNS was first standardized, though, there was one query type that didn’t really have any semantic meaning:

Pattern matching primates

Why do we see faces where there are none? Paradolia
Why do we look at random noise and see patterns? Patternicity
Why do we think we have discovered what’s causing filtering if we change one thing and email gets through?
It’s all because we’re pattern matching primates, or as Michael Shermer puts it “people believe weird things because of our evolved need to believe nonweird things.”
Our brains are amazing and complex and filter a lot of information so we don’t have to think of it. Our brains also fill in a lot of holes. We’re primed at seeing patterns, even when there’s no real pattern. Our brains can, and do, lie to us all the time. For me, some of the important part of my Ph.D. work was learning to NOT trust what I thought I saw, and rather to effectively observe and test. Testing means setting up experiments in different ways to make it easier to not draw false conclusions.
Humans are also prone to confirmation bias: where we assign more weight to things that agree with our preconceived notions.
Take the email marketer who makes a number of changes to a campaign. They change some of the recipient targeting, they add in a couple URLs, they restructure the mail to change the text to image ratio and they add the word free to the subject line. The mail gets filtered to the bulk folder and they immediately jump to the word free as the proximate cause of the filtering. They changed a lot of things but they focus on the word free.
Then they remove the word free from the subject line and all of a sudden the emails are delivering. Clearly the filter in question is blocking mail with free in the subject line.
Well, no. Not really. Filters are bigger and more complex than any of us can really understand. I remember a couple years ago, when a few of my close friends were working at AOL on their filter team. A couple times they related stories where the filters were doing things that not even the developers really understood.
That was a good 5 or 6 years ago, and filters have only gotten more complex and more autonomous. Google uses an artificial neural network as their spam filter. I don’t really believe that anything this complex just looks at free in the subject line and filters based on that.
It may be that one thing used to be responsible for filtering, but those days are long gone. Modern email filters evaluate dozens or hundreds of factors. There’s rarely one thing that causes mail to go to the bulk folder. So many variables are evaluated by filters that there’s really no way to pinpoint the EXACT thing that caused a filter to trigger. In fact, it’s usually not one thing. It could be any number of things all adding up to mean this may not be mail that should go to the inbox.
There are, of course, some filters that are one factor. Filters that listen to p=reject requests can and do discard mail that fails authentication. Virus filters will often discard mail if they detect a virus in the mail. Filters that use blocklists will discard mail simply due to a listing on the blocklist.
Those filters address the easy mail. They leave the hard decisions to the more complex filters. Most of those filters are a lot more accurate than we are at matching patterns. Us pattern matching primates want to see patterns and so we find them.