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OOPS!

Y’know those days when it seems everything goes wrong? And you just can’t get it right? A couple companies who send commercial mail have had a day like that.
Yesterday I got an email at 6am from a vendor telling me there was a new, important update to download and install. I put it off because it’s software I don’t use very often and I’m waiting until we have a better idea of our hardware situation before loading too much stuff on my backup laptop. Three hours later, I got another email from the vendor telling me that the link in the email was wrong and here was the right link and they’re sorry for the bad email initially.
Fair enough, stuff breaks and process falls apart and sometimes there are customer facing screw ups. But this vendor wasn’t done! This morning I got a third email telling me that uh, the previous emails were only intended to go out to their Windows using customers, and that the didn’t currently have a Mac version of the software ready. And, well, they’ll email me as soon as they get the Mac version finished.
I made a comment about bad day for mailers and Steve pointed out that he’d gotten 3 different notifications from a shipping company and then a final fourth email that said the company was testing things and they’re sorry for sending multiple test messages out to their whole list this morning.
It’s not even Friday the 13th or anything.

Forcing those opens

Most email marketers want to see their open rates go up. This particular marketer has come up with a new way to force recipients to load their mail.

Getting rid of the via at Gmail

There was a question submitted today about the verification process at Gmail.

Inbox rates and conversion rates

Jeanne Jennings published an interesting bit of research on open rates and inbox rates at ClickZ recently. Essentially she looked at two different industry studies and compared their results.
The first study was the Return Path Global Delivery Survey and the second was the Epsilon North American Trend Results. What Jeanne found is that while Return Path shows a decrease in inbox placement, Epsilon is seeing an increase in average open rate.

There are any number of reasons this could be happening, including simply different ways the numbers are calculated. I am not sure it’s just a numbers issue, though. Many of Epsilon’s clients are very big companies with a very experienced marketing team. The Return Path data is across their whole user base, which is a much broader range of marketers at different levels of sophistication.
I expect that the Epsilon data is a subset of the Return Path data, and a subset at the high end at that. It does hint, though, that when the inbox is less cluttered, recipients are more likely to open the commercial mail that does get in there.

Ask Ben Lerer anything

Ben Lerer, the co-founder of Thrillist, will be doing an “Ask Me Anything” on Reddit on Tuesday at 10 am.
What is an Ask me Anything? It’s a free wheeling discussion where someone agrees to answer any questions from anyone who posts on Reddit.
Who is Ben Lerer? Ben is the co-founder of Thrillist, a quite successful email business. I worked with Thrillist early on in their business. Their blend of quirky editorials and irreverence drive a very engaged recipient base and great email delivery. Join them tomorrow on Reddit to ask him anything.
Update: Here’s Ben’s AMA.

Spamtraps mean your list is bad

Spamtraps on a list are a symptom, not the disease itself. They’re (usually) a sign of some serious underlying problem, whether it be with address capture, bounce management, list purchase or epending.
We’ve talked about this a lot in the past, but sometimes you need a short summary to refer someone to.

77% prefer email for marketing

77% of those surveyed preferred email for permission-based promotional messages, soundly beating the next most popular, direct mail, at 9%. Email, still anything but dead.
This, and lots of other interesting things, in ExactTarget’s 2012 Channel Preference Survey.

The 500 mile email

This is a great story from Trey Harris about a real email delivery issue from the mid 1990s.
Here’s a problem that sounded impossible… I almost regret posting the story to a wide audience, because it makes a great tale over drinks at a conference. 🙂 The story is slightly altered in order to protect the guilty, elide over irrelevant and boring details, and generally make the whole thing more entertaining.
I was working in a job running the campus email system some years ago when I got a call from the chairman of the statistics department.
“We’re having a problem sending email out of the department.”
“What’s the problem?” I asked.
“We can’t send mail more than 500 miles,” the chairman explained.
I choked on my latte. “Come again?”
“We can’t send mail farther than 500 miles from here,” he repeated. “A little bit more, actually. Call it 520 miles. But no farther.”
“Um… Email really doesn’t work that way, generally,” I said, trying to keep panic out of my voice. One doesn’t display panic when speaking to a department chairman, even of a relatively impoverished department like statistics. “What makes you think you can’t send mail more than 500 miles?”
“It’s not what I think,” the chairman replied testily. “You see, when we first noticed this happening, a few days ago–”
“You waited a few DAYS?” I interrupted, a tremor tinging my voice. “And you couldn’t send email this whole time?”
“We could send email. Just not more than–”
“–500 miles, yes,” I finished for him, “I got that. But why didn’t you call earlier?”
“Well, we hadn’t collected enough data to be sure of what was going on until just now.” Right. This is the chairman of *statistics*. “Anyway, I asked one of the geostatisticians to look into it–”
“Geostatisticians…”
“–yes, and she’s produced a map showing the radius within which we can send email to be slightly more than 500 miles. There are a number of destinations within that radius that we can’t reach, either, or reach sporadically, but we can never email farther than this radius.”
“I see,” I said, and put my head in my hands. “When did this start? A few days ago, you said, but did anything change in your systems at that time?”
“Well, the consultant came in and patched our server and rebooted it. But I called him, and he said he didn’t touch the mail system.”
“Okay, let me take a look, and I’ll call you back,” I said, scarcely believing that I was playing along. It wasn’t April Fool’s Day. I tried to remember if someone owed me a practical joke.
I logged into their department’s server, and sent a few test mails. This was in the Research Triangle of North Carolina, and a test mail to my own account was delivered without a hitch. Ditto for one sent to Richmond, and Atlanta, and Washington. Another to Princeton (400 miles) worked.
But then I tried to send an email to Memphis (600 miles). It failed. Boston, failed. Detroit, failed. I got out my address book and started trying to narrow this down. New York (420 miles) worked, but Providence
(580 miles) failed.
I was beginning to wonder if I had lost my sanity. I tried emailing a friend who lived in North Carolina, but whose ISP was in Seattle. Thankfully, it failed. If the problem had had to do with the geography of the human recipient and not his mail server, I think I would have broken down in tears.
Having established that–unbelievably–the problem as reported was true, and repeatable, I took a look at the sendmail.cf file. It looked fairly normal. In fact, it looked familiar.
I diffed it against the sendmail.cf in my home directory. It hadn’t been altered–it was a sendmail.cf I had written. And I was fairly certain I hadn’t enabled the “FAIL_MAIL_OVER_500_MILES” option. At a loss, I telnetted into the SMTP port. The server happily responded with a SunOS sendmail banner.
Wait a minute… a SunOS sendmail banner? At the time, Sun was still shipping Sendmail 5 with its operating system, even though Sendmail 8 was fairly mature. Being a good system administrator, I had standardized on Sendmail 8. And also being a good system administrator, I had written a sendmail.cf that used the nice long self-documenting option and variable names available in Sendmail 8 rather than the cryptic punctuation-mark codes that had been used in Sendmail 5.
The pieces fell into place, all at once, and I again choked on the dregs of my now-cold latte. When the consultant had “patched the server,” he had apparently upgraded the version of SunOS, and in so doing downgraded Sendmail. The upgrade helpfully left the sendmail.cf alone, even though it was now the wrong version.
It so happens that Sendmail 5–at least, the version that Sun shipped, which had some tweaks–could deal with the Sendmail 8 sendmail.cf, as most of the rules had at that point remained unaltered. But the new long configuration options–those it saw as junk, and skipped. And the sendmail binary had no defaults compiled in for most of these, so, finding no suitable settings in the sendmail.cf file, they were set to zero.
One of the settings that was set to zero was the timeout to connect to the remote SMTP server. Some experimentation established that on this particular machine with its typical load, a zero timeout would abort a connect call in slightly over three milliseconds.
An odd feature of our campus network at the time was that it was 100% switched. An outgoing packet wouldn’t incur a router delay until hitting the POP and reaching a router on the far side. So time to connect to a lightly-loaded remote host on a nearby network would actually largely be governed by the speed of light distance to the destination rather than by incidental router delays.
Feeling slightly giddy, I typed into my shell:

The Physics of the Email Universe

We talk a lot about rules and best practices in email, but we’re mostly talking about “squishy” rules-of-thumb that are based on simplified models of how mail systems, spam filters, recipients, postmasters and blacklist operators behave. They’re the biology, ecology and sociology of the email ecosystem.
There’s another set of rules we tend to only mention in passing, if at all, though. They’re the steely, sharp-edged laws that control the email universe. They’re the RFCs that define how email works and make sure that mail systems written by hundreds of different people across the globe all work and all interoperate with each other.
Building a message from Zeros and Ones
RFC 5322 – Internet Message Format
This tells you everything you need to know about crafting a simple email, with a subject line, a sender, some recipients and a simple plain-text message. It’s also the foundation of all fancier emails. If you’re creating emails, this is where to start.
A little more than plain ASCII
RFC 2047 – MIME Part 3: Message Header Extensions for Non-ASCII Text
RFC 2047 is one small part of the MIME (Multipurpose Internet Mail Extensions) suite of protocols that allow you to include pictures and attachments and prettily formatted text and comic sans in your email. This part defines how you can put things other than the plainest of plain text in your subject lines or in the “friendly from” of your message. It’s what allows you to put Hiragana, or Cyrillic, or umlauts, or cedillas, or properly matched double quotes in your subject line. It also let’s you put hearts or smiley faces or other little pictograms there – but nothing this useful is going to be perfect.
RFC 2045 – MIME Part 1: Format of Internet Message Bodies
This shows how to send an image, or a plain text mail in a different character set, or an HTML mail. It doesn’t tell you how to send plain text and HTML, or to send HTML with embedded images, or a message with an attached document. For that you need…
Finally, Modern Email
RFC 2046 – MIME Part 2: Media Types
This builds on RFC 2045 to allow you to have many different chunks in a message – this is what you need if you want to send “proper” HTML mail with a plain text alternative, or if you want embedded images or attachments.
Getting From A To B
RFC 5321 – Simple Mail Transfer Protocol
A message isn’t much use unless you send it somewhere. RFC 5321 explains the mysteries of actually sending that message over the wire to the recipient. If you need to know about the different phases of a message delivery, what “4xx” and “5xx” actually mean, why there’s not really any such thing as a hard or soft bounce defined, just temporary or permanent failures, or anything else about actually sending mail or diagnosing mail delivery, this is your starting point.
The Rest Of The Iceberg
I’ve only touched on the very smallest tip of the email iceberg here. There’s much, much more – both in RFCs and ad-hoc non-RFC standards. If you’re interested in more, this is a decent place to start.

Best Practices: your mileage may vary

YMMV. One of those abbreviations us old folks used ages ago before email had pictures and the closest we had to social networking was USENET and social gaming was in the form of MUDs. I rarely see it used any more. In a lot of ways that’s a sad thing. It was a very useful abbreviation. Using it at the end of a post full of advice was a sign that the author was providing information but knew that different situations may require different solutions. It acknowledged that what might be the best practice in one form may not be the best for another.
It’s not just the usage that seems to have declined, there seem to be a lot more people who just want to share The Answer! and not acknowledge their experience may not be universal. This seems particularly rampant in email marketing, at least to me (YMMV).
I’ve talked before about how I don’t believe there are any universal best practices for email.
Let’s be honest, the experience of a well known national retailer buying, or appending email addresses is not going to be the same as a local business doing the same thing. The national retailer acquiring email addresses and sending well targeted mail to their purchasers probably won’t cause too many delivery problems, and will generate revenue. The local pizza place probably won’t be so lucky.
A number of marketers have complained that they all too often hear “it depends” when they ask a question about email. But how well a particular email campaign perform does depend. Success depends on the audience and the offer. But more than just the specific offer, success also depends on how well known the brand is and what their real world reputation with customers is.
Customers are a lot more likely to give brands the benefit of the doubt if they like the product. That means poor practices don’t always result in poor results. It also means other companies may not have the same success with poor practices.
Your Mileage May Vary.