Things you need to read: 2/5/16

gearheadAsk the Expert: How Can Email Marketers Stay Out of Gmail Jail and in the Inbox? The expert in question is an old friend of mine, Andrew Barrett. I met Andrew online in the late 90s, and we worked together (briefly) at MAPS. He was out of email for a while, but I’m pleased he came back to share his talents with us. The information in the article is valuable for anyone who struggles with getting to the Gmail inbox.
Unclutter Your Inbox, Archive & Keep Your Messages. Shiv Shankar talks about some new features at Yahoo Mail. With a simple click, you can archive email so it’s available to search, but not cluttering up your inbox. One of the things that jumped out at me from that article is that Yahoo is providing 1 TB of storage. That’s more than Google!
The EEC is doing a survey on the impact of CASL and want to hear from marketers. Go check out their blog post and take their survey.
Sparkpost has a guest blog from Alex Garcia-Tobar, co-founder of Valimail about common DKIM failures. I’ve met Alex a few times and I’ve always found him a pleasure to talk to. Alex is somewhat new in the email space, but he really gets some of the challenges in the authentication space. A lot of the issues he mentions in that blog post like lack of key rotation and shared keys are some of the technical debt I was talking about in my predictions for 2016 post.
What links have you read this week that are worth sharing?

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Gmail FBL update

Last week Gmail started contacting ESPs that signed up for their new FBL with more information on how to set up mailings to receive FBL emails.
One of the struggles some ESPs are having is the requirement for DKIM signing. Many of the bigger ESPs have clients that sign with their own domains. Gmail is telling these ESPs to insert a second DKIM signature to join the FBL.
There are a couple reasons this is not as simple or as doable as Gmail seems to think, and the challenges are technical as well as organizational.
The technical challenges are pretty simple. As of now, not all the bulk MTAs support multiple signatures. I’ve heard that multiple signatures are being tested by these MTA vendors, but they’re not in wide use. This makes it challenging for these ESPs to just turn on multiple signatures. For ESPs that are using open source software, there’s often a lot of customization in their signing infrastructure. Even if they have the capability to dual sign, if they’re not currently using that there is testing needed before turning it on.
None of the technical challenges are show stoppers, but they are certainly show delayers.
The organizational challenges are much more difficult to deal with. These are cases where the ESP customer doesn’t want the ESP to sign. The obvious situation is with large banks. They want everything in their infrastructure and headers pointing at the bank, not at their ESP. They don’t want to have that second signature in their email for multiple reasons. I can’t actually see an ESP effectively convincing the various stakeholders, including the marketing, security and legal staff, that allowing the ESP to inset a second signature is good practice. I’m not even sure it is good practice in those cases, except to get stats from Gmail.
Hopefully, Gmail will take feedback from the ESPs and change their FBL parameters to allow ESPs to get information about their customers who sign with their own domain.

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May 2014: The month in email

It’s been a busy and exciting month for us here.
Laura finished a multi-year project with M3AAWG, the Messaging, Malware and Mobile Anti-Abuse Working Group (look for the results to be published later this year) and continued working with clients on interesting delivery challenges and program opportunities. Steve focused on development on the next version release of Abacus, our flagship abuse desk tool, which will also be available later this year.
And as always, we had things to say about email.
The World of Spam and Email Best Practices
We started the month with a bit of a meta-discussion on senders’ fears of being labeled spammers, and reiterated what we always say: sending mail that some people don’t want doesn’t make you evil, but it is an opportunity to revisit your email programs and see if there are opportunities to better align your goals with the needs of people on your email lists. We outlined how we’ve seen people come around to this position after hitting spamtraps. That said, sometimes it is just evil. And it’s still much the same evil it’s been for over a decade.
We also wrote a post about reputation, which is something we get asked about quite frequently. We have more resources on the topic over at the WiseWords section of our site.
Gmail, Gmail, Gmail
Our friends over at Litmus estimate Gmail market share at 12%, which seems pretty consistent with the percentage of blog posts we devote to the topic, yes? We had a discussion of Campaign Monitor’s great Gmail interview, and offered some thoughts on why we continue to encourage clients to focus on engagement and relevance in developing their email programs. We also wrote a post about how Gmail uses filters, which is important for senders to understand as they create campaigns.
SMTP and TLS
Steve wrote extensively this month about the technical aspects of delivery and message security. This “cheat sheet” on SMTP rejections is extremely useful for troubleshooting – bookmark it for the next time you’re scratching your head trying to figure out what went wrong.
He also wrote a detailed explanation of how TLS encryption works with SMTP to protect email in transit, and followed that with additional information on message security throughout the life of the message. This is a great set of posts to explore if you’re thinking about security and want to understand potential vulnerabilities.
DKIM
Steve also wrote a series of posts about working with DKIM (DomainKeys Identified Mail), the specification for signing messages to identify and claim responsibility for messages. He started with a detailed explanation of DKIM Replay Attacks, which happens when valid email is forwarded or otherwise compromised by spammers, phishers or attackers. Though the DKIM signature persists (by design) through a forward, the DKIM specification restricts an attacker’s ability to modify the message itself. Steve’s post describes how senders can optimize their systems to further restrict these attacks. Another way that attackers attempt to get around DKIM restrictions is by injecting additional headers into the message, which can hijack a legitimately signed message. If you’re concerned about these sort of attacks (and we believe you should be), it’s worth learning more about DKIM Key Rotation to help manage this. (Also of note: we have some free DKIM management tools available in the WiseTools section of our site.)
As always, we’re eager to hear from you if there are topics you’d like us to cover in June.

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ISPs speak at M3AAWG

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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