Troubleshooting delivery is hard, but doable

Even for those of us who’ve been around for a while, and who have a lot of experience troubleshooting delivery problems things are getting harder. It used to be we could identify some thing about an email and if that thing was removed then the email would get to the inbox. Often this was a domain or a URL in the message that was triggering bulk foldering.
Filters aren’t so simple now. And we can’t just randomly send a list of URLs to a test account and discover which URL is causing the problem. Sure, one of the URLs could be the issue, but that’s typically in context with other things. It’s rare that I can identify the bad URLs sending mail through my own server these days.
There are also a lot more “hey, help” questions on some of the deliverability mailing lists. Most of these questions are sticky problems that don’t map well onto IP or domain reputation.
One of my long term clients recently had a bad mail that caused some warnings at Gmail.
We tried a couple of different things to try and isolate the problem, but never could discover what was triggering the warnings. Even more importantly, we weren’t getting the same results for identical tests done hours apart. After about 3 days, all the warnings went away and all their mail was back in the inbox.
It seemed that one mailing was really bad and resulted in a bad reputation, temporarily. But as the client fixed the problem and kept mailing their reputation recovered.
Deliverability troubleshooting is complicated and this flowchart sums up what it’s like.

Here at Word to the Wise, we get a lot of clients who have gone through the troubleshooting available through their ESPs and sometimes even other deliverability consultants. We get the tough cases that aren’t easy to figure out.
What we do is start from the beginning. First thing is to confirm that there aren’t technical problems, and generally we’ll find some minor problems that should be fixed, but aren’t enough to cause delivery problems. Then we look at the client’s data. How do they collect it? How do they maintain it? What are they doing that allows false addresses on their list?
Once we have a feel for their data processes, we move on to how do we fix those processes. What can we do to collect better, cleaner data in the future? How can we improve their processes so all their recipients tell the ISP that this is wanted mail?
The challenging part is what to do with existing data, but we work with clients individually to make sure that bad addresses are expunged and good addresses are kept.
Our solutions aren’t simple. They’re not easy. But for clients who listen to us and implement our recommendations it’s worth it. Their mail gets into the inbox and deliverability becomes a solved problem.

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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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When did the reject happen?

conversation_for_blogEarlier today I approved a comment from Mike on a post about problems at AOL from 2012. The part of the comment that caught my attention:

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Truths and Myths about email deliverability

virtualShow_forblogKen Magill will be interviewing me on the Truths and Myths of Email Deliverability, November 12 at the 2015 All About eMail Virtual Conference & Expo. Ken has a bunch of questions he wants to ask me, but he’s also expecting to take a lot of questions from the audience as well.
Speaking of myths, there has been discussion lately about recycled spamtraps. Apparently, there are people who believe (believed?) that every ISP uses recycled spamtraps. When Hotmail and Gmail said recently they didn’t use recycled traps people got very upset that they believed something that was not true.
It’s a mess. There is so much about email that is like a version of telephone. One person says “hotmail uses recycled spamtraps” someone else repeats “big ISPs use recycled spamtraps” then then third person says “all ISPs use recycled spamtraps.” People try and correct this type of misinformation all the time but sometimes it’s hard to clarify.
So show up to our session and let Ken lob questions at me, lob some of your own and we can see what myths we can clear up.

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