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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Guide to resolving ISP issues

I often get a chuckle out of watching some people, who are normally on the blocking end of the delivery equation, struggle through their own blocking issues. A recent situation came up on a mailing list where someone who has very vehement opinions about how to approach her particular blocklist for delisting and that the lists policies are immutable. The company she works for is having some delivery issues and she’s looking for a contact to resolve the issues.
While digging through my blog posts to see if there was any help I could provide, I realized I don’t have a guide to resolving blocking issues at ISPs. Much of the troubleshooting can be done without ever contacting the ISPs or the blocklists.
Identify the issue.
There are a number of techniques that ISPs use to protect their users from malicious or problematic mail, from rate-liming incoming mail, putting mail in the bulk folder, or blocking specific IP addresses. Step one to resolving any delivery problem is to identify what is happening to the mail. In order to resolve the issue, you have to know what the issue is.
All too often, the description of a delivery problem is: My mail isn’t getting delivered. But that isn’t very clear as to what the actual problem is. Are you being temp failed? Is mail being blocked? Is mail going to the bulk folder? Is this something affecting just you or is it a widespread problem?
Troubleshoot your side.
Collect as much data about the problem as you can. Dig through logs and get copies of any rejection messages. Follow any URLs that are present in the bounce messages. Try sending a bare bones email to yourself at that ISP with just URLs, is it still blocked? What if you send from a different IP, does the same thing happen?
There is a lot of troubleshooting a sender can do without having to contact an ISP, and the information can lead to resolution that doesn’t involve having to contact the ISP. Also, many current ISP blocks are dynamic, they come up and go down without any human intervention. Those blocks that require contact to get them resolved have clear instructions in the bounce message.
Fix your stuff.
Whether it’s a reputation issue or a minor technical issue, fix the problem on your end. Just moving IP addresses or changing a URL isn’t a sustainable fix. There is a reason mail is being blocked or filtered and if you don’t fix that issue, the blocks are just going to come back. After you do fix your stuff, expect to see changes in a few days or a week. The ISP filters are generally quite responsive to sender improvements so if you’ve fixed the stuff you should see changes pretty quickly. Expect unblocking or filtering to take a little longer than the block was in place.
If you can’t figure out what the problem is, hire a consultant. Here at Word to the Wise we can often quickly identify a problem and provide a path to resolution. Sometimes the problem isn’t even the ISPs, we’ve had multiple cases where our clients were using custom software and their software wasn’t SMTP compliant and we were able to identify the problem and get their mail working again. There are a host of other independent consultants out there that can also help you identify and resolve blocking problems.
Contact the ISPs.
If there is a hard block or after fixing what you think the underlying problem is, you’ll have to contact the ISP. Many ISPs provide self service websites and contact forms to facilitate this process. Generally, though, most issues aren’t going to require contact.

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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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FBox: The sky isn't falling

Having listened to the Facebook announcement this morning, I am even more convinced that emailpocalypse isn’t happening.
Look, despite the fact that companies like Blue Sky Factory think that this means marketers are NEVER EVER going see the inside of an inbox again this isn’t the end of email marketing.
Yes, Facebook email is a messaging platform that marketers are not going to have direct, unlimited and unfettered access to. I have no problem with this. Unfettered access to a messaging platform has been abused by marketers long enough, that I heartily approve of a platform that gives real control back to the recipient.
With that being said, there are a couple blindingly obvious ways to avoid having to give users control of their own inbox.

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