Ask Laura: Is the SmartScreen Filter Really Smart?

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Dear Laura,
Can you help me understand the Microsoft SmartScreen filter? I’m working on a new project and we’re not able to get to the inbox at Microsoft. 
Our SNDS/JMRP health is great, not a problem that we can see, but when we contact the support team we’re told we’re being flagged by SmartScreen. It seems impossible to try and find any information or ways to rectify this issue. We’re not blacklisted, and our deliverability and open rates with other providers is generally solid. Any ideas?
Signed, Is SmartScreen actually Smart?

Dear Signed,
SmartScreen is a proprietary Microsoft measurement for email. The SmartScreen filter is based on a number of things Microsoft collects from their users. Like many mail providers, Microsoft looks at how users interact with mail, including deleting without reading, moving to the spam folder, moving from the spam folder, saving, and marking as spam. In addition to these standard metrics, Microsoft also directly asks users their opinion on mail.
The Microsoft panel is different than many other filtering technologies, and is worth spending a little time discussing. Microsoft selects users of any of their different webmail systems at random and invites them to be part of their panel. After users agree to be on the panel, some of the mail they are receiving is presented to them in a special window. The users are asked if this is spam or not spam.
There are a couple things to remember about the Microsoft Panel data.

  • Panelists are chosen at random.
  • Panelists are only asked about mail that is addressed to them.
  • Microsoft considers this data more accurate than other measurements.
  • ReturnPath customers can get a glimpse into the panel data, but otherwise this is not shared.

If you’re being told by support that it’s a SmartScreen flag, then the underlying problem is your reputation. Recipients are directly telling Microsoft that they don’t like your mail and there are other negative impacts from the subscribers.
Getting out of SmartScreen filters can be a significant challenge for senders. The underlying issue, as with many deliverability issue, is the recipients. My most successful clients have temporarily purged their lists down to just very engaged recipients. Once mail was going to the inbox, they made decisions about which users to add back to the mail stream and then did so.
Overall, if you’re seeing problems with SmartScreen, the solution is to go back to the beginning and look at your permission and data collection practices.
laura

When we work with brands and senders to improve email delivery, there are many questions that come up again and again. For 2016, we thought it might be interesting to answer some of those questions here on the blog so others can benefit from the information.
Confused about delivery in general? Trying to keep up on changing policies and terminology? Need some Email 101 basics? This is the place to ask. We can’t answer specific questions about your server configuration or look at your message structure for the column (please get in touch if you’d like our help with more technical or forensic investigations!), but we’d love to answer your questions about how email works, trends in the industry, or the joys and challenges of cohabiting with felines.

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Email predictions for 2015

Welcome to a whole new year. It seems the changing of the year brings out people predicting what they think will happen in the coming year. It’s something I’ve indulged in a couple times over my years of blogging, but email is a generally stable technology and it’s kind of boring to predict a new interface or a minor tweak to filters. Of course, many bloggers will go way out on a limb and predict the death of email, but I think that’s been way over done.
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Even major technical advancements, like authentication protocols and the rise of IPv6, are not usually sudden. They’re discussed and refined through the IETF process. While some of these changes may seem “all of a sudden” to some end users, they’re usually the result of years of work from dedicated volunteers. The internet really doesn’t do flag days.
One major change in 2014, that had significant implications for email as a whole, was a free mail provider abruptly publishing a DMARC p=reject policy. This caused a lot of issues for some small business senders and for many individual users. Mailing list maintainers are still dealing with some of the fallout, and there are ongoing discussions about how best to mitigate the problems DMARC causes non-commercial email.
Still, DMARC as a protocol has been in development for a few years. A number of large brands and commercial organizations were publishing p=reject policies. The big mail providers were implementing DMARC checking, and rejection, on their inbound mail. In fact, this rollout is one of the reasons that the publishing of p=reject was a problem. With the flip of a switch, mail that was once deliverable became undeliverable.
Looking back through any of the 2014 predictions, I don’t think anyone predicted that two major mailbox providers would implement p=reject policies, causing widespread delivery failures across the Internet. I certainly wouldn’t have predicted it, all of my discussions with people about DMARC centered around business using DMARC to protect their brand. No one mentioned ISPs using it to force their customers away from 3rd party services and discussion lists.
I think the only constant in the world of email is change, and most of the time that change isn’t that massive or sudden, 2014 and the DMARC upheaval notwithstanding.
But, still, I have some thoughts on what might happen in the coming year. Mostly more of the same as we’ve seen over the last few years. But there are a couple areas I think we’ll see some progress made.

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Last week at M3AAWG representatives from AOL, Yahoo, Gmail and Outlook spoke about their anti-spam technologies and what the organizations were looking for in email.
This session was question and answers, with the moderator asking the majority of the questions. These answers are paraphrased from my notes or the MAAWG twitter stream from the session.
What are your biggest frustrations?
AOL: When senders complain they can’t get mail in and we go look at their stats and complaints are high. Users just don’t love that mail. If complaints are high look at what you may have done differently, content does have an effect on complaints.
Outlook: When we tightened down filters 8 years ago we had to do it. Half of the mail in our users inbox was spam and we were losing a steady number of customers. The filter changes disrupted a lot of senders and caused a lot of pain. But these days only 0.5% of mail in the inbox is spam.  Things happen so fast, though, that the stress can frustrate the team.
Gmail: Good senders do email badly sometimes and their mail gets bulked. Senders have to get the basic email hygiene practices right. Love your users and they’ll love you back.
What’s your philosophy and approach towards mail?
AOL: There is a balance that needs to be struck between good and bad mail. The postmaster team reminds the blocking team that not all mail is bad or malicious. They are the sender advocates inside AOL. But the blocking team deals with so much bad mail, they sometimes forget that some mail is good.
Yahoo: User experience. The user always comes first. We strive to protect them from malicious mail and provide them with the emails they want to see. Everything else is secondary.
Gmail: The faster we stop spam the less spam that gets sent overall. We have highly adaptive filters that can react extremely quickly to spam. This frustrates the spammers and they will give up.
Outlook: The core customer is the mailbox user and they are a priority. We think we have most of the hardcore spam under control, and now we’re focused on personalizing the inbox for each user. Everyone online should hold partners accountable and they should expect to be held accountable in turn. This isn’t just a sender / ESP thing, ISPs block each other if there are spam problems.
What are some of your most outrageous requests?
We’ve been threatened with lawsuits because senders just don’t want to do the work to fix things. Some senders try to extort us. Other senders go to the advertising execs and get the execs to yell at the filtering team.
Coming to MAAWG and getting cornered to talk about a particular sender problem. Some senders have even offered money just to get mail to the spam folder.
Senders who escalate through the wrong channels. We spent all this money and time creating channels where you can contact us, and then senders don’t use them.
Confusing business interests with product interests. These are separate things and we can’t change the product to match your business interest.
What are your recommendations for changing behaviors?
Outlook: We provide lots of tools to let you see what your recipients are doing. USE THE TOOLS. Pay attention to your recipient interaction with mail. Re-opt-in recipients periodically. Think about that mail that is never opened. Monitor how people interact with your mail. When you have a problem, use our webpages and our forms. Standard delivery problems have a play book. We’re going to follow that playbook and if you try to get personal attention it’s going to slow things down. If there’s a process problem, we are reachable and can handle them personally. But use the postmaster page for most things.
Gmail: Get your hygiene right. If you get your hygiene right, deliverability just works. If you’re seeing blocking, that’s because users are marking your mail as spam. Pay attention to what the major receivers publish on their postmaster pages. Don’t just follow the letter of the law, follow the spirit as well. Our responsibility, as an ISP, is to detect spam and not spam. Good mailers make that harder on us because they do thinks that look like spammers. This doesn’t get spammer mail in more, it gets legitimate mail in less. Use a real opt-in system, don’t just rely on an implied opt-in because someone made a purchase or something.
Yahoo: ESPs are pretty good about screening their customers, so pay attention to what your ESPs are saying. Send mail people want. Verify that the email addresses given to you actually belong to people who want your mail. Have better sender practices.
What do you think about seed accounts?
The panel wasn’t very happy about the use of seed accounts. Seeds are not that useful any longer, as the ISPs move to more and more personalized delivery. Too much time and too many cycles are used debugging seed accounts. The dynamic delivery works all ways.
When things go wrong what should we do?
AOL: Open a ticket. We know we’ve been lax recently, but have worked out of our backlog and are caught up to date. Using the ticketing system also justifies us getting more headcount and makes everyone’s experience better. Also, don’t continue what you’re doing. Pausing sending while you’re troubleshooting the issue. We won’t adjust a rep for you, but we may be able to help you.
Gmail: Do not jump the gun and open a ticket on the first mail to the spam folder. Our filters are so dynamic, they update every few minutes in some cases. Be sure there is a problem. If you are sure you’re following the spirit and letter of the sender guidelines you can submit a ticket. We don’t respond to tickets, but we work every single one. When you’re opening a ticket provide complete information and full headers, and use the headers from your own email address not headers from a seed account. Give us a clear and concise description of the problem. Also, use the gmail product forum, it is monitored by employees and it’s our preferred way of getting information to the anti-abuse team. Common issues lots of senders are having will get addressed faster.
Outlook: Dig in and do your own troubleshooting, don’t rely on us to tell you what to fix. The support teams don’t have a lot of resources so use our public information. If you make our job harder, then it takes longer to get things done. But tell us what changes you’ve made. If you’ve fixed something, and tell us, our process is different than if you’re just asking for a delisting or asking for information. When you’ve fixed things we will respond faster.
How fast should users expect filters to respond after making changes?
Filters update continually so they should start seeing delivery changes almost immediately. What we find is people tell us they’ve made changes, but they haven’t made enough or made the right ones. If the filters don’t update, then you’ve not fixed the problem.

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