Content

Another way Gmail is different

I was answering a question on Mailop earlier today and had one of those moments of clarity. I finally managed to articulate one of the things I’ve known about Gmail, but never been able to explain. See, Gmail has never really put a lot of their filtering on the SMTP transaction and IP reputation. Other ISPs do a lot of the heavy lifting with IP filters. But not Gmail.
While I was writing the answer I realized something. Gmail was a late entrant into the email space. AOL, Hotmail, Yahoo, even the cable companies, were providing email services in the 90s. When spam started to be a problem, they started with IP based blocking. As technology got better and content filtering became viable, improvements were layered on top of IP based blocking.

Gmail didn’t enter the mailbox market until the 2000’s. When they did, they had money, lots of hardware, and internal expertise to do content filtering. They didn’t start with IP based filtering, so their base is actually content filtering. Sure, there were some times when they’d push some mail away from the MTAs, but most of their filtering was done after the SMTP transaction. The short version of this is I never really pay any attention to IP reputation when dealing with Gmail. It’s just another factor. Unless you’re blocked and if you get blocked by Gmail, wow, you really screwed up.
Gmail does, of course, do some IP based blocking. But in my experience IP filters are really only turned against really egregious spam, phishing and malicious mail. Most email marketers reading my blog won’t ever see IP filters at Gmail because their mail is not that bad.
Other companies aren’t going to throw away filters that are working, so the base of their filters are IPs. But Google never had that base to work from. Their base is content filters, with some IP rep layered on top of that.
That’s a big reason Gmail filters are different from other filters.

Are you blocking yourself?

One thing that catches me up with clients sometimes is their own spam filters block their own content. It happens. In some cases the client is using an appliance. The client’s reputation is bad enough that the appliance actually blocks mail. Often these clients have no idea they are blocking their own mail, until we try and send them something and the mail is rejected.

Typically, the issue is their domains are the problem. We mention the domains in email, and the filters do what filters do. We work around this by abbreviating the domains or calling, it’s not a big deal.
It’s a great demonstration of content filters, though. The content (the client’s domain) is blocked even when it comes from an IP with a good reputation. In fact, with Gmail I can often tell “how bad” a domain reputation is. Most mail I send from WttW to my gmail address goes to the inbox, even when the client is reporting bulk foldering at Gmail. But every once in a while a domain has such a bad reputation that any mail mentioning that domain goes to bulk.
Most folks in the deliverability space know the big players in the filtering market: Barracuda, Cloudmark, ProofPoint, etc. Those same people have no idea what filters their company uses and have never even really thought about it.
Do you know what filter your company is using to protect employees from spam?

Thoughts from #EEC16

EEC16 was my first Email Experience conference. I was very impressed. Dennis, Len, and Ryan put together a great program. I made it to two of the keynotes and both took me out of an email focused place to look at the bigger picture.

Patrick Scissons discussed his experiences creating marketing and advertising campaigns for good and to share messages. Some of the campaigns were ones I’d seen as a consumer, or on the news. One of the campaigns he talked about specifically was for the group Moms Demand Action, looking at sensible gun control in the US. The images and symbology used in those campaigns were striking and very effective.
Kelly McEvers talked about her experiences as a correspondent in the middle east during the Arab Spring. She is an engaging speaker, as one who does radio should be. Her overall message and theme was that sometimes events are such that you need to throw the list away and go with it. As someone who lives by “the list” and tries to make sure I’m prepared for every eventuality I found that a very useful message. Particularly when throwing away “the list” turned into some massively successful stories.
In terms of sessions, I found the email content session fascinating. I blogged about content in email last week and did some live tweeting, too. What really hit me after that session was that good marketing drives deliverability. Everything that Carey Kegel was talking about in terms of better marketing, sounded like things I recommend to clients to drive deliverability.
Back in 2012 I was writing posts about how delivery and marketing were somewhat at odds with each other. The premise was that marketing was about creating mindshare, and repeating a message so often a recipient couldn’t forget it. In email, repetition can cause recipient fatigue and drive delivery problems. But what I’m hearing now, from the leading minds of email marketers, is that email marketing works better if you send relevant and useful information to consumers. Recipients are key and you can’t just keep hammering them, you have to provide them with some value.
It seems marketing has finally come around to the delivery point of view.

March 2016: The Month In Email

Happy April! I’m just back from the EEC conference in New Orleans, which was terrific. I wrote a quick post about a great session on content marketing, and I’ll have more to add about the rest of the conference over the next week or so. Stay tuned!

Here’s a look at what caught our attention in March:
On the DMARC front, we noted that both Yahoo and mail.ru are moving forward with p=reject, and Steve offered some advice for ESPs and software developers on methods for handling this gracefully. I also answered an Ask Laura question about making the decision to publish DMARC. Look for more on that in this month’s Ask Laura questions…
Our other Ask Laura question this month was about changing ESPs, which senders do for many reasons. It’s useful to know that there will generally be some shifts in deliverability with any move. Different ESPs measure engagement in different ways, and other issues may arise in the transition, so it’s good to be aware of these if you’re contemplating a change.
In industry news, I wrote a sort of meta-post about how the Internet is hard (related: where do you stand on the great Internet vs. internet debate? Comment below!) and we saw several examples of that this month, including a privacy debacle at Florida State University. Marketing is hard, too. I revisited an old post about a fraud case where a woman sued Toyota over an email marketing “prank”. As always, my best practices recommendation for these sorts of things (and everything else!) really boils down to one thing: send wanted email.
Steve wrote extensively about SPF this month in two must-read posts, where he explained the SPF rule of ten and how to optimize your SPF records. He also wrote about Mutt, the much-loved command line email client, and marked the passing of industry pioneer Ray Tomlinson, who, in addition to his many accomplishments, was by all accounts a very thoughtful and generous man.
Finally, I occasionally like to take a moment and follow the twisty paths that lead to my spam folder. Here’s a look at how Ugg spams my email doppelganger, MRS LAURA CORBISHLEY. In other spam news, there’s a lot of very interesting data in the recent 10 Worst list from Spamhaus. Take a look if you haven’t seen it yet.

Content is the new volume!

I’m having a great time here at #EEC16. Today is my visit and go to sessions day, since tomorrow I’m speaking at 2 different sessions.
I was lucky enough to get into the Customer Experience session presented by Carey Kegel of SmartPak and Loren McDonald of IBM Marketing Cloud. It was an interesting session.
If you don’t know, SmartPak is a brand focused on selling horse tack and supplements. They initially started off by creating packs of supplements for your horse. This is great for horse owners, as it means the barn staff just needs to add one pack to your horse’s feed. No measuring, no confusion, it’s simple and means your horse gets what they need.
First they started talking about the volume of email sent by SmartPak. Their mails aren’t that consistent, but they mail between 25 and 30 emails a month. Some months last year they mailed every day.
What they started seeing, though, is that the volume of marketing mail drove list churn. The biggest reason users gave for unsubscribing was “too much volume.” The more mail they sent, the more unsubscribes they saw. Even worse, more volume did not translate into revenue. As email volume went up, email performance decreased.
They tested adding content to emails. Just a block on the side of the email with links to content on their website. Adding the content links increased click through rates by 9% and revenue per email by 15%.
These results don’t require the content be in the emails. Using emails to drive recipients to already existing content on the website, including videos and surveys.
The session didn’t specifically discuss deliverability directly, but I think there were some clear deliverability benefits to content marketing. In fact, an email with no call to action, simply a post-purchase “what to expect” email had an open rate of 33%. These types of open rates help improve overall reputation and lead to more inbox deliveries.

The session really drove home how valuable content marketing is. One thing that was continually repeated during the session is that most marketers have the content already. Use email to drive users to the content you already have. Include that content in marketing mails. Meet the recipient’s needs and wants.
There are a couple takeaways I got from the session.

January 2015 – The Month in Email

It’s February already! January went fast, right? At WttW, we are gearing up for MAAWG SF later this month — will we see you there?
We started the year with a set of predictions about email. Mostly we think email will continue to be great at some things and not-so-great at other things, and we’ll keep fighting the good fight to make it better.
As always, I’m interested in filters and how spammers continue to work around them to reach the inbox. I also wrote about how the language of an email impacts delivery, and wrote an expanded response to a comment suggesting email filters should be illegal. You can guess where I stand on that (and if you can’t, perhaps you might read more about how email is an inherently malicious traffic stream…)
I also took a moment to point out a trend I’m really enjoying, which is the rise of content marketing (a.k.a. giving customers useful and interesting information they can’t find elsewhere). As I said in the post, I’ll be curious to see how ROI plays out with this strategy.
We also talked about some of the less exciting content we see in email, notably the infamous Murkowski Statement, by which a spammer declares “Nope! Nothing to see over here!”
Steve also pointed out some content shenanigans in the form of hidden preview text, with some additional clarification from the original marketer in the comments.
In industry news, the big story was that Microsoft has partially implemented DMARC for Office365, and was the first to make a public statement about the specific ways they’ve chosen to implement. In my post, I did a walkthrough of a message to illustrate a bit about how this works, which might be useful if you’re trying to wrap your head around DMARC implementations.
We also talked about consolidation in the ESP space, and got a number of comments from readers about who they think might be next. Shortly thereafter, Listcast was acquired by MailerMailer.
Josh noted a few major shutdowns: Yahoo China email services and the AHBL list. The latter explores the challenges inherent in decommissioning a blacklist, and there’s a good discussion in the comments, so you might check it out if you missed that earlier this month.
Josh also pointed to the Salesforce State of Marketing report, which is always a useful set of metrics about how marketers are using email and other channels. It’s definitely worth a read.

Content based filtering

Content filtering is often hard to explain to people, and I’m not sure I’ve yet come up with a good way to explain it.
A lot of people think content reputation is about specific words in the message. The traditional content explanation is that words like “Free” or too many exclamation points in the subject line are bad and will be filtered. But it’s not the words that are the issue it’s that the words are often found in spam. These days filters are a lot smarter than to just look at individual words, they look at the overall context of the message.
ISP_tolerances
Even when we’re talking content filters, the content is just a way to identify mail that might cause problems. Those problems are evaluated the same way IP reputation is measured: complaints, engagement, bad addresses. But there’s a lot more to content filtering than just the engagement piece. What else is part of content evaluation?

Horses, not zebras

I was first introduced to the maxim “When you hear hoofbeats, think horses not zebras” when I worked in my first molecular biology lab 20-some-odd years ago. I’m no longer a gene jockey, but I still find myself applying this to troubleshooting delivery problems for clients.
It’s not that I think all delivery problems are caused by “horses”, or that “zebras” never cause problems for email delivery. It’s more that there are some very common causes of delivery problems and it’s a more effective use of time to address those common problems before getting into the less common cases.
This was actually something that one of the mailbox provider reps said at M³AAWG in SF last month. They have no problem with personal escalations when there’s something unusual going on. But, the majority of issues can be handled through the standard channels.
What are the horses I look for with delivery problems.

The death of IP based reputation

Back in the dark ages of email delivery the only thing that really mattered to get your email into the inbox was having a good IP reputation. If your IP sent good mail most of the time, then that mail got into the inbox and all was well with the world. All that mattered was that good IP reputation. Even better for the people who wanted to game the system and get their spam into the inbox, there were many ways to get around IP reputation.
Every time the ISPs and spam filtering companies would work out a way to block spam using IP addresses, spammers would figure out a way around the problem. ISPs started blocking IPs so spammers moved to open relays. Filters started blocking open relays, so spammers moved to open proxies. Filters started blocking mail open proxies so spammers created botnets. Filters started blocking botnets, so spammers started stealing IP reputation by compromising ESP and ISP user accounts. Filters were constantly playing catchup with the next new method of getting a good IP reputation, while still sending spam.
While spammers were adapting and subverting IP based filtering a number of other things were happening. Many smart people in the email space were looking at improving authentication technology. SPF was the beginning, but problems with SPF led to Domains Keys and DKIM. Now we’re even seeing protocols (DMARC) layered on top of DKIM. Additionally, the price of data storage and processing got cheaper and data mining software got better.
The improvement in processing power, data mining and data storage made it actually feasible for ISPs and filtering companies to analyze content at standard email delivery speeds. Since all IPv4 addresses are now allocated, most companies are planning for mail services to migrate to IPv6. There are too many IPv6 IPss to rely on IP reputation for delivery decisions.
What this means is that in the modern email filtering system, IPs are only a portion of the information filters look at when making delivery decisions. Now, filters look at the overall content of the email, including images and URLs. Many filters are even following URLs to confirm the landing pages aren’t hosting malicious software, or isn’t content that’s been blocked before. Some filters are looking at DNS entries like nameservers and seeing if those nameservers are associated with bad mail. That’s even before we get to the user feedback, in the form of “this is spam” or “this is not spam” clicks, which now seem to affect both content, domain and IP reputation.
I don’t expect IP reputation to become a complete non-issue. I think it’s still valuable data for ISPs and filters to evaluate as part of the delivery decision process. That being said, IP reputation is so much less a guiding factor in good email delivery than it was 3 or 4 years ago. Just having an IP with a great reputation is not sufficient for inbox delivery. You have to have a good IP reputation and good content and good URLs.
Anyone who wants good email delivery should consider their IP reputation, but only as one piece of the delivery strategy. Focusing on a great IP reputation will not guarantee good inbox delivery. Look at the whole program, not just a small part of it.

Confirmation is too hard…

One of the biggest arguments against confirmation is that it’s too hard and that there is too much drop off from subscribers. In other words, recipients don’t want to confirm because it’s too much work on their part.
I don’t actually think it’s too much work for recipients. In fact, when a sender has something the recipient wants then they will confirm.
A couple years ago I was troubleshooting a problem. One of my client’s customer was seeing a huge percentage of 550 errors and I was tasked with finding out what they were doing. The first step was identifying the source of the email addresses. Turns out the customer was a Facebook app developer and all the addresses (so he told me) were from users who had installed his apps on Facebook. I did my own tests and couldn’t install any applications without confirming my email address.
Every Facebook user that has installed an application has clicked on an email to confirm they can receive email at the address they supplied Facebook. There are over 1 billion users on Facebook.
Clicking a link isn’t too hard for people who want your content. I hear naysayers who talk about “too hard” and “too much drop off” but what they’re really saying is “what I’m doing isn’t compelling enough for users to go find the confirmation email.”
This isn’t to say everyone who has a high drop off of confirmations is sending poor content. There are some senders that have a lot of fake, poor or otherwise fraudulent addresses entered into their forms. In many cases this is the driving factor for them using COI: to stop people from using their email to harass third parties. Using COI in these cases is a matter of self protection. If they didn’t use COI, they’d have a lot of complaints, traps and delivery problems.
The next time you hear confirmation is too hard, remember that over 1 billion people, including grandparents and the technologically challenged, managed to click that link to confirm their Facebook account. Sure, they wanted what Facebook was offering, but that just tells us that if they want it bad enough they’ll figure out how to confirm.
HT: Spamresource

Mail that looks good on desktop and mobile

Over the weekend I noticed a new CSS framework aimed at email rather than web development, “Antwort“.
This isn’t the first or only framework for email content, but this one looks simple and robust, and it allows for content that doesn’t just adapt for different sized displays but looks good on all of them. The idea behind it is to divide your content into columns, magazine style, then display the columns side-by-side on desktop clients and top to bottom on mobile clients. That opens up much more interesting designs than the more common single fluid column approach.

It looks nice, it supports pretty much every interesting email client, but it also comes with some directions based on real world experience.

Thanks for your questions!

Thanks, everyone, who submitted questions to laura-questions@wordtothewise.com. We’ve gotten some great questions to answer here on the blog. I’m working through the emails and contacting folks if I have questions. I’ll be answering the first question on Wednesday.
I also did have someone harvest the address off the website and send me non-CAN SPAM compliant spam to it. I have to admit, I didn’t expect someone to harvest the address at all, but especially not within 12 hours of posting an address. Particularly someone who’s not harvested our contact address previously. I also am considering how much content I could get detailing taking the spammer to court in CA for violating CAN SPAM and the CA anti-spam statute.

Return Path on Content Filtering

Return Path have an interesting post up about content filtering. I like the model of 3 different kinds of filters, in fact it’s one I’ve been using with clients for over 18 months. Spamfiltering isn’t really about one number or one filter result, it’s a complex interaction of lots of different heuristics designed to answer the question: do recipients want this kind of mail?

Things Spammers Do

Much like every other day, I got some spam today. Here’s a lightly edited copy of it.
Let’s go through it and see what they did that makes it clear that it’s spam, which companies helped them out, and what you should avoid doing to avoid looking like these spammers…

Delivery challenges increasing

Return Path published their most recent Global Deliverability report this morning. (Get the Report) This shows that inbox placement of mail has decreased 6% in the second half of 2011. This decrease is the largest decrease Return Path has seen in their years of doing this report.
To be honest, I’m not surprised at the decrease. Filters are getting more sophisticated. This means they’re not relying on simply IP reputation for inbox delivery any longer. IP reputation gets mail through the SMTP transaction, but after that mail is subject to content filters. Those content filters are getting a lot better at sorting out “wanted” from “unwanted” mail.
I’m also hearing a lot of anecdotal reports that bulk folder placements at a couple large ISPs increased in the first quarter of 2012. This is after the RP study was finished, and tells me increased bulk folder placement is more likely to be a trend and not a blip.
One of the other interesting things from the RP study is that the differences are not across all mail streams, but are concentrated in certain streams and they vary across different regions.

Content, trigger words and subject lines

There’s been quite a bit of traffic on twitter this afternoon about a recent blog post by Hubspot identifying trigger words senders should avoid in an email subject line. A number of email experts are assuring the world that content doesn’t matter and are arguing on twitter and in the post comments that no one will block an email because those words are in the subject line.
As usually, I think everyone else is a little bit right and a little bit wrong.
The words and phrases posted by Hubspot are pulled out of the Spamassassin rule set. Using those words or exact phrases will cause a spam score to go up, sometimes by a little (0.5 points) and sometimes by a lot (3+ points). Most spamassassin installations consider anything with more than 5 points to be spam so a 3 point score for a subject line may cause mail to be filtered.
The folks who are outraged at the blog post, though, don’t seem to have read the article very closely. Hubspot doesn’t actually say that using trigger words will get mail blocked. What they say is a lot more reasonable than that.

Looking towards the future

I had the opportunity to go to a seminar and networking event hosted by Return Path yesterday evening. The topic was “Email trends in 2012” and it was presented by Tom Sather.
If any of you get the opportunity to go to a talk presented by any of the Return Path folks I encourage you to do so. They know their stuff and their presentations are full of good information.
One of the trends mentioned is the increase in reliance on domain reputation. It’s something I’ve been thinking about more and more recently. I wrote a little bit about it recently, but have focused more on the whole realm of content filtering rather than just domain reputation.
Domain reputation is where delivery is going. And I think a lot of senders are going to struggle with delivery as they find that IP reputation is not enough to get into the inbox.

Email marketing ulcers for the holiday

I’ve mentioned here before that I can usually tell when the big ISPs are making changes to their spam filtering as that ISP dominates my discussions with current and potential clients and many discussions on delivery mailing lists.
The last two weeks the culprit has been Yahoo. They seem to be making a lot of changes to their filtering schemes right at the busiest email marketing time of the year. Senders are increasing their volume trying to extract that last little bit of cash out of holiday shoppers, but they’re seeing unpredictable delivery results. What worked to get mail into the inbox a month ago isn’t working, or isn’t working as well, now.
Some of this could be holiday volume related. Many marketers have drastically increased their mail volume over the last few weeks. But I don’t think the whole issue is simply that there is more email marketing flowing into our mailboxes.
As I’ve been talking with folks, I have started to see a pattern and have some ideas of what may be happening. It seems a lot of the issue revolves around bulk foldering. Getting mail accepted by the MXs seems to be no different than it has been. The change seems to be based on the reputation of the URLs and domains in the email.
Have a domain with a poor reputation? Bulk. Have a URL seen in mail people aren’t interested in? Bulk. Have a URL pointing to a website with problematic content? Bulk.
In the past IPs that were whitelisted or had very good reputations could improve delivery of email with neutral or even borderline poor reputations. It seems that is no longer an effect senders can rely on. It may even be that Yahoo, and other ISPs, are going to start splitting IP reputation from content reputation. IP reputation is critical for getting mail in the door, and without a good IP reputation you’ll see slow delivery. But once the mail has been accepted, there’s a whole other level of filtering, most of it on the content and generally unaffected by the IP reputation.
I don’t think the changes are going to go away any time soon. I think they may be refined, but I do think that reputation on email content (particularly domains and URLs and target IP addresses) is going to play a bigger and bigger role in email delivery.
What, specifically, is going to happen at Yahoo? Only they can tell you and I’m not sure I have enough of a feel for the pattern to speculate about the future. I do think that it’s going to take a few weeks for things to settle down and be consistent enough that we can start to poke the black box and map how it works.

Content based filters

Content based filters are incredibly complex and entire books could be written about how they work and what they look at. Of course, by the time the book was written it would be entirely obsolete. Because of their complexity, though, I am always looking for new ways to explain them to folks.
Content based filters look at a whole range of things, from the actual text in the message, to the domains, to the IP addresses those domains and URLs point to. They look at the hidden structure of an email. They look at what’s in the body of the message and what’s in the headers. There isn’t a single bit of a message that content filters ignore.
Clients usually ask me what words they should change to avoid the filters. But this isn’t the right question to ask. Usually it’s not a word that causes the problem. Let me give you a few examples of what I mean.
James H. has an example over on the Cloudmark blog of how a single missing space in an email caused delivery problems for a large company. That missing space changed a domain name in the message sufficiently to be caught by a number of filters. This is one type of content filter, that focuses on what the message is advertising or who the beneficiary of the message is. Some of my better clients get caught by these types of filters occasionally. A website they’re linking to or a domain name they’re using in the text of the message has a bad reputation. The mail gets bulked or blocked because of that domain in the message.
One of my clients went from 100% inbox every day to random failures at different domains. Their overall inbox was still in the 96 – 98% range, but there was a definite change. The actual content of their mail hadn’t changed, but we kept looking for underlying causes. At one point we were on the phone and they mentioned their new content management system. Sure enough, the content management company had a poor reputation and the delivery problems started exactly when they started using the content management. The tricky part of this was that the actual domains and URLs in the messages never changed, they were still clickthrough.clientdomain.example.com. But those URLs now pointed to an IP address that a lot of spammers were abusing. So there were delivery problems. We made some changes to their setup and the delivery problems went away.
The third example is one from quite a long time ago, but illustrates a key point. A client was testing email sends through a new ESP. They were sending one-line mail through the ESPs platform to their own email account. Their corporate spamfilter was blocking the mail. After much investigation and a bit of string pulling, I finally got to talk to an engineer at the spamfiltering company. He told me that they were blocking the mail because it “looked like spam.” When pressed, he told me they blocked anything that had a single line of text and an unsubscribe link. Once the client added a second line of text, the filtering issue went away.
These are just some of the examples of how complex content based filters are. Content is almost a misnomer for them, as they look at so many other things including layout, URLs, domains and links.

Sharing content, sharing reputation

Over at SpamResource Al talks about how sharing content is like sharing needles.