Anyone know why…

Countless questions about email troubleshooting start with “does anyone know why.” Unfortunately, most of these questions don’t contain enough detail to get a useful answer.

In the case of email, even the smallest redactions, like the IP address and the domain in question, can make it difficult for anyone to provide help. Details matter.
Every detail matters, sending IP and domain are just the beginning. Who’s doing the sending? What is their authentication setup? What IP are they using? How were the addresses collected? What is their frequency? What MTA is used? Are they linking to outside sites? Are they linking to outside services? Where are images hosted?  Is the mail going to the bulk folder or being rejected? What ISPs or filters are involved?
The relevant questions go on and on and on.
We send fairly detailed question lists to clients. I regularly look at them to try and make them shorter. But the reality is these are questions that are relevant. Without enough information we simply cannot troubleshoot delivery problems.
 

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Microsoft is still in the process of rolling out new mail servers. One thing that is new about these is some new codes on their error messages. This has led to questions and speculations as to what is going on.

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Troubleshooting email delivery

Mark Brownlow has a post up explaining how he discovered some problems with delivery at Gmail by digging deeper into his statistics. Mark goes through his thought process including his initial conjecture on what might be causing the problems and then how he looked at the data to see if his supposition fit the data.
I love this post. It is so refreshing to watch someone document how they asked questions, then looked at data to find out the answers. Too many people treat best practices in email delivery as a set of rules that are meant to be broken. Instead of actually asking questions and determining what is best for their market and their recipients they implement best practices.
Following best practices isn’t exactly a bad thing, the reason they’re best is because they’re easy to communicate practices that will not result in bad outcomes. But, they’re not always the ideal practices for a specific situation. Best practices are ones that work across a wide range of senders and situations. Blindly implementing best practices will not always result in the best outcome for each situation.
Mark’s post is a tutorial in the art of looking at email delivery. I think there is a need for more of those kinds of posts, explaining the process from identifying an email problem through to confirming that is actually the problem and then testing potential fixes. I’ll be posting troubleshooting guides here over the next few weeks and months. If you have an issue you think would be an interesting case study drop me an email and we’ll go through it.

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Where do you accept reports?

One of the things that is most frustrating to me about sending in spam reports is that many ESPs and senders don’t actively monitor their abuse address. A few months ago I talked about getting spam from Dell to multiple email addresses of mine.
What I didn’t talk about was how badly broken the ESP was in handling my complaint. The ESP was, like many ESPs, an organization that grew organically and also purchased several smaller ESPs over the course of a few years. This means they have at least 5 or 6 different domains.
The problem is, they don’t effectively monitor abuse@ for those different domains. In fact, it took me blogging about it to get any response from the ESP. Unfortunately, that initial response was “why didn’t you tell us about it?”
I pointed out I’d tried abuse@domain1, abuse@domain2, abuse@domain3, and abuse@domain4. Some of the addresses were in the mail headers, others were in the ESP record at abuse.net. Three of those addresses bounced with “no such user.” In other words, I’d tried to tell them, but they weren’t accepting reports in a way I could access.
Every ESP should have active abuse addresses at domains that show up in their mail. This means the bounce address domain should have an abuse address. The reverse DNS domain should have an abuse address. The d= domain should have an abuse address.
And those addresses should be monitored. In the Dell case, the ESP did have an active abuse@ address but it was handled by corporate. Corporate dropped the ball and never forwarded the complaint to the ESP reps who could act on the spam issue.
ESPs and all senders should have abuse@ addresses that are monitored. They should also be tested on a regular basis. In the above case, addresses that used to work were disabled during some upgrade or another. No one thought to test to see if they were working after the change.
You should also test your process. If you send in a complaint, how does it get handled? What happens? Do you even have a complaint handling process outside of “count and forward”?
All large scale senders should have appropriate abuse@ addresses that are monitored. If you don’t, well, you look like a spammer.

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