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.

BlueHornet spun off from Digital River
What do you think about these hot button issues?

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Thoughts on "ISP relations"

I’ve been thinking a lot about the field of ISP relations and what it means and what it actually is. A few years ago the answer was pretty simple. ISP relations is about knowing the right people at ISPs in order to get blocks lifted.
The fact that ISPs had staff just to deal with senders was actually a side effect of their anti-spam efforts. In many places blocking was at least partially manual, so there had to be smart, technical, talented people to handle both the blocking and unblocking. That meant there were people to handle sender requests for unblocking.
Spam filters have gotten better and more sophisticated. Thus, the ISPs don’t need smart, technical, talented and expensive people in the loop. Most ISPs have greatly scaled back their postmaster desks and rely on software to handle much of the blocking.
Another issue is that some people on the sender side rely too heavily on the ISPs for their data. This makes the ISP reps, and even some spam filtering company reps, reluctant to provide to much help to senders. I’ve had at least 3 cases in the last 6 months where a sender contacted me to tell me they had spoken with someone at an ISP or filtering company and were told they would get no more help on a particular issue. In talking with those reps it was usually because they were drowning under sender requests and had to put some limits on senders.
All of this means ISP Relations is totally different today than it was 5 years ago. It’s no longer about knowing the exact right person to contact. Rather it’s about being able to identify problems without ISP help. Instead of being able to ask someone for information, ISP Relations specialists need to know how to find data from different sources and use that data to identify blocking problems. Sure, knowing the right person does help in some cases when there’s an obscure and unusual issue. But mostly it’s about putting together any available evidence and then creating a solution.
We still call it “ISP Relations” but at a lot of ISPs there is no one to contact these days. I think the term is a little misleading, but it seems to be what we’re stuck with.

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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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#EME15 and visiting Stockholm

Last month I had the pleasure of presenting a couple talks to APSIS customers at their Email Marketing Evolved conference in Stockholm. The first talk was about deliverability and how it’s changed over the years. The second was about looking at the future of email and communicating with users online as we move forward in the digital world.
The rest of the post is going to be a bit photo heavy, so here’s a cut tag.

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