August 2017: The month in email

Hello! Hope all are keeping safe through Harvey, Irma, Katia and the aftermath. I know many people that have been affected and are currently out of their homes. I am proud to see so many of my fellow deliverability folks are helping our displaced colleagues with resources, places to stay and money to replace damaged property.
Here’s a mid-month late wrapup of our August blog posts. Our favorite part of August? The total eclipse, which was absolutely amazing. Let me show you some pictures.





Ok, back to email.
We’re proud of the enormous milestone we marked this month: ten years of near-daily posts to our Word to the Wise blog. Thanks for all of your attention and feedback over the past decade!
In other industry news, I pointed to some interesting findings from the Litmus report on the State of Email Deliverability, which is always a terrific resource.
I also wrote about the evolution of filters at web-based email providers, and noted that Gmail’s different approach may well be because it entered the market later than other providers.
In spam, spoofing, and other abuse-related news, I posted about how easy it is for someone to spoof a sender’s identity, even without any technical hacks. This recent incident with several members of the US presidential administration should remind us all to be more careful with making sure we pay attention to where messages come from. How else can you tell that someone might not be wholly legitimate and above-board? I talked about some of what I look at when I get a call from a prospective customer as well as some of the delightful conversations I’ve had with spammers over the years.
In the security arena, Steve noted the ongoing shift to TLS and Google’s announcement that they will label text and email form fields on pages without TLS as “NOT SECURE”. What is TLS, you ask? Steve answers all your questions in a comprehensive post about Transport Layer Security and Certificate Authority Authorization records.
Also worth reading, and not just for the picture of Paddington Bear: Steve’s extremely detailed post about local-part semantics, the chunk of information before the at sign in an email address. How do you choose your email addresses (assuming they are not assigned to you at work or school…)? An email address is an identity, both culturally and for security purposes.
In subscription best practices — or the lack thereof — Steve talked about what happens when someone doesn’t quite complete a user registration. Should you send them a reminder to finish their registration? Of course! Should you keep sending those reminders for 16 months after they’ve stopped engaging with you? THE SURPRISING ANSWER! (Ok, you know us. It wasn’t that surprising.)

Google Postmaster bad IP reputation
Targeted advertising

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Are you (accidentally) supporting phishing

One of the themes in some of my recent talks has been how some marketers teach their customers to become victims of phishing. Typically I’m talking about how companies register domains “just for email” and then use those for bulk messages. If customers get used to mail from company.ESP.com and companyemail.com they’re going to believe that company-email.com is also you.
There are other ways to train your customers to be phishing victims, too. Zeltzer security walks us through a couple emails that look so much like phishing that it fooled company representatives. Go take a read, they give a number of examples of both good and bad emails.
biohazardmail
I was a little frustrated that the examples don’t include headers so we could look at the authentication. But the reality is only a teeny, tiny fraction of folks even know how to check headers. They’re not very useful for the average user.
Security is something we should never forget. As more and more online accounts are tied to our email addresses those of us who market to email addresses need to think about what we’re teaching our recipients about our company. DMARC and other authentication technologies can help secure email, but marketers also need to pay attention to how they are communicating with recipients.

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Email pranks and spoofing

Earlier today a twitter user calling himself Email Prankster released copies of email conversations with various members of the current US administration. Based on his twitter feed, and articles from BBC News and CNN, it appears that the prankster forged “friendly from” names in emails to staffers.
A bunch of folks will jump on this bandwagon and start making all sorts of claims about how this kind of thing would be prevented if the Whitehouse and other government offices would just implement DMARC. Problem is, that’s not true. It wouldn’t have helped at all in this case. Looking at the email screenshots all of the mail seems to come from legitimately registered addresses at free email providers like mail.com, gmail.com, and yandex.com.
One image indicates that some spam filter noticed there may be a problem. But apparently SUSPECTED_SPAM in the subject line wasn’t enough to make recipients think twice about checking the email.

The thing is, this is not “hacking” and this isn’t “spear phishing” and it’s not even really spoofing. It’s social engineering, at best. Maybe.

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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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