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Email marketing is hard

I’ve watched a couple discussions around the email and anti-spam community recently with a bit of awe. It seems many email marketers are admitting they are powerless to actually implement all the good advice they give to others.
They are admitting they can’t persuade, cajole, influence or pressure their companies to actually follow best practices. Some of the comments public and private comments I’ve heard from various industry leaders:

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Guaranteed email delivery

Ben over at Mailchimp has a good post about his response (and his support staff’s more professional and helpful response) to inquires asking if Mailchimp can guarantee an improvement in delivery.
I sympathize with Ben, and commend his staff. I often get potential clients asking me if I can guarantee I can get their mail to the inbox or get them off a public or private blocklist. And, the answer really is no, I can’t guarantee anything. Much of delivery is solely in the hands of the actual sender. Sure, ESPs can enforce a certain standard of behaviour and they can do all the technical things right. And consultants like me can tell you how ISP spam filters work and explain how some of your choices and processes affect delivery. But none of us can guarantee inbox delivery.
Only one company has tried to guarantee inbox delivery, and they shut down earlier this year because they were non-viable and couldn’t get enough of a recipient userbase to attract customers.
For the rest of us, though, the best we can do is give senders the tools and information they need to succeed in getting mail delivered to the inbox.

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Content based filtering

A spam filter looks at many things when it’s deciding whether or not to deliver a message to the recipients inbox, usually divided into two broad categories – the behaviour of the sender and the content of the message.
When we talk about sender behaviour we’ll often dive headfirst into the technical details of how that’s monitored and tracked – history of mail from the same IP address, SPF records, good reverse DNS, send rates and ramping, polite SMTP level behaviour, DKIM and domain-based reputation and so on. If all of those are OK and the mail still doesn’t get delivered then you might throw up your hands, fall back on “it’s content-based filtering” and not leave it at that.
There’s just as much detail and scope for diagnosis in content-based filtering, though, it’s just a bit more complex, so some delivery folks tend to gloss over it. If you’re sending mail that people want to receive, you’re sure you’re sending the mail technically correctly and you have a decent reputation as a sender then it’s time to look at the content.
You want your mail to look just like wanted mail from reputable, competent senders and to look different to unwanted mail, viruses, phishing emails, botnet spoor and so on. And not just to mechanical spam filters – if a postmaster looks at your email, you want it to look clean, honest and competently put together to them too.
Some of the distinctive content differences between wanted and unwanted email are due to the content as written by the sender, some of them are due to senders of unwanted email trying to hide their identity or their content, but many of them are due to the different quality software used to send each sort of mail. Mail clients used by individuals, and content composition software used by high quality ESPs tends to be well written and complies with both the email and MIME RFCs, and the unwritten best common practices for email composition. The software used by spammers, botnets, viruses and low quality ESPs tends not to do so well.
Here’s a (partial) list of some of the things to consider:

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