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Deliverability, email and lessons learned from Insight2015

biohazardmailDeliverability is a challenge, I think everyone who has ever tried to send bulk mail will acknowledge that. There are a lot of reasons for this. One of the big reasons is that there are bad players who spend a lot of time trying to get around filters. And a lot of these people are sending very bad mail. Phishing. Spear Phishing. Viruses. Malware.
Email is a prime vector for a lot of criminals.
A lot of deliverability discussions really gloss over the dangers, though. We don’t often think about it, because we’re not sending bad mail. But we still have to go through the same filters that ask: Is this message safe?
Security was a big deal at the recent Sparkpost / MessageSystems conference.

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November 2015: The month in email

As we head into the last month of the year, we look back at our November adventures. I spoke twice this month, first at Message Systems Insight in Monterey (my wrap-up post is here) and then with Ken Magill at the  at the 2015 All About eMail Virtual Conference & Expo (a short follow-up here, and a longer post on filters that came out of that discussion here.). Both were fun and engaging — it’s always great to get a direct sense of what challenges are hitting people in the email world, and to help clear up myths and misconceptions about what works and doesn’t work in email marketing and delivery. I’m putting together my conference and speaking schedule for 2016 — if you know of anything interesting that should be on my radar, please add it in the comments, thanks!
In industry news, we noted a sharp uptick in CBL listings, and then posted about the explanation for the false positives. Steve wrote about an interesting new Certificate Authority (CA) called Let’s Encrypt, which looks to be a wonderful (and much-needed) alternative for certificates, and I put together some thoughts on SenderScore.
Steve and I did a few posts in parallel this month. First, Steve posted an interesting exercise in SPF debugging. Are you seeing mail from legitimate senders flagged as spam? This might be why. My investigative post was about ISP rejections, and how you can figure out where the block is occurring. In each case, you’ll get a glimpse of how we go about identifying and troubleshooting issues, even when we don’t have much to go on.
We each also wrote a bit about phishing. Steve posted a timely warning about spear phishing — malware attacks disguised as legitimate email from within your organization — and reminds all of us to be careful about attachments. With all of the more secure options for document sharing these days, it’s a lot easier to avoid the risk by maintaining a no-attachments policy in your company. And I wrote about how the Department of Defense breaking HTML links in email to help combat phishing. If your lists include military addresses (.mil), you may want to come up with a strategy for marketing to those recipients that relies less on a clickthrough call to action.
We amused ourselves a bit with a game of Deliverability Bingo, then followed up with a more serious look at the thing we hear all the time — “I’m sure they’ll unblock me if I can just explain my business model.” While an ESP abuse desk is unlikely to be swayed by this strategy, it is actually at the core of how we think about deliverability at Word to the Wise. Legitimate senders have many kinds of lists, many kinds of recipients, many kinds of marketing strategies, and many kinds of business goals. For us to help marketers craft sustainable email programs, we need to understand exactly what matters most to our clients.

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All About Email: Q & A session tomorrow

virtualShow_forblogLive! Tomorrow! the 2015 All About eMail Virtual Conference & Expo. 12:30 Eastern, 9:30 Pacific. Come hear Ken ask me about email and contribute your own questions!
Want to ask about spamtraps? Purchased lists? How about engagement? Just want to listen to what myths other people are interested in asking about? Come and listen.
 

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