Troubleshooting: part 3

As I continue to think about how people troubleshoot email delivery I keep finding other things to talk about. Today we’re going to talk about the question most folks start with when troubleshooting delivery. “Did ISP change something?”

image of a head with gears and ideas floating around it

At least once a week I check some delivery or email fora and some form of the question is sitting there.

“Did X change something? We haven’t done anything different and our delivery went way down overnight.”

Did Y change their filters? Our delivery is tanking and all our authentication is fine.”

Anyone hear of a change at Z? We have been having increasing difficulty reaching the inbox and we don’t understand why. Looking for suggestions.

In reality, the answer to this question Does Not Matter and asking it is only going to delay actually resolving your delivery issue.

When filters change

The reality is, filters are continually changing. ISPs and filtering companies are always tuning filters. These changes are roughly in 3 categories.

  • Ongoing tweaking and improvement to provide a better experience for their users
  • Changes done to address a emergent threat (Yahoo deploying p=reject is one example of this)
  • Specific changes to catch a type of spam they had previously been unable to effectively identify and filter.

Filters are not static. They are continually adjusting based on a number of things. We can always assume the answer to the question is yes. Something changed. Now what?

There are basically 3 situations here.

  • The filters did something unexpected and caught mail it wasn’t intended to catch, causing recipients to complain to the ISP.
  • The filter change was intentional but caught more mail than was intended, causing recipients to complain to the ISP.
  • The filter change was intentional and caught exactly the mail that was intended and the recipients didn’t care enough to notice that mail was missing.

In the first two cases, the ISP is going to fix things. They’re going to listen to their users and adjust the filters. In the first case, I expect to see changes and rollback within 24 – 48 hours. In the second, I expect to see changes in 24 – 96 hours.

The third case is the interesting one. Does anyone care about mail they don’t care about going to the bulk folder? Folks sending mail, even opt-in mail, that the users don’t complain about when it’s missing is the definition of grey mail. Filter maintainers listen to their users. If users complain they’ll change things, if users don’t complain they’ll assume the filters are working as intended.

The answer to the question did the filters changed tells you nothing. Of course the filters changed. Either they’re doing something that the maintainers don’t intend, which means they’ll be fixed or they’re catching mail they’re intended to catch.

Instead of asking if the filters changed, flip the question. Why are my users not interested enough in my mail to notice it when it’s gone? Start your troubleshooting from that perspective.

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Email filters and small sends

Have you heard about the Baader-Meinhoff effect?

The Baader-Meinhof effect, also known as frequency illusion, is the illusion in which a word, a name, or other thing that has recently come to one’s attention suddenly seems to appear with improbable frequency shortly afterwards (not to be confused with the recency illusion or selection bias). Baader–Meinhof effect at Wikipedia

There has to be an corollary for email. For instance, over the last week or so I’ve gotten an influx of questions about how to fix delivery for one to one email. Some have been from clients “Oh, while we’re at it… this happened.” Others have been from groups I’m associated with “I sent this message and it ended up in spam.”

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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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Troubleshooting delivery problems

Everyone has their own way of troubleshooting problems. I thought I would list out the steps I take when I’m trying to troubleshoot them.

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