Thanks for the great session

I had a great time answering questions at the 2015 All About eMail Virtual Conference & Expo today. Thanks so much to everyone who participated and asked questions. They were great and I’m sorry we didn’t have more time.
I did get some questions on twitter (@wise_laura) afterwards. One was about an example I gave to explain how filters are complex. There have been rumors going around recently that Gmail is filtering mail with more than 3 URLs in it. Let me just say right now THIS IS NOT TRUE emails with more than 3 URLs in them are being delivered just fine to Gmail.
There is a situation involving the number (and type) of URLs that I think are a useful example of the filter complexity happening at some places, like Gmail. I started working on it, but don’t quite have time to finish it today, but will keep working on and it should go up in the next day or so.
Thanks again to everyone who joined the session. You asked some great questions and I had fun answering them.
 

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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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SPF debugging

Someone mentioned on a mailing list that mail “from” intuit.com was being filed in the gmail spam folder, with the warning “Our systems couldn’t verify that this message was really sent by intuit.com“. That warning means that Gmail thinks it may be phishing mail. Given they’re a well-known financial services organization, I’m sure there is a lot of phishing mail claiming to be from them.
But I’d expect that a company the size of Intuit would be authenticating their mail, and that Gmail should be able to use that authentication to know that the mail wasn’t a phish.
Clearly something is broken somewhere. Lets take a look.
Looking at the headers, the mail was being sent from Salesforce, and (despite Salesforce offering DKIM) it wasn’t DKIM signed by anyone. So … look at SPF.
SPF passes:

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Why do ISPs do that?

One of the most common things I hear is “but why does the ISP do it that way?” The generic answer for that question is: because it works for them and meets their needs. Anyone designing a mail system has to implement some sort of spam filtering and will have to accept the potential for lost mail. Even the those recipients who runs no software filtering may lose mail. Their spamfilter is the delete key and sometimes they’ll delete a real mail.
Every mailserver admin, whether managing a MTA for a corporation, an ISP or themselves inevitably looks at the question of false positives and false negatives. Some are more sensitive to false negatives and would rather block real mail than have to wade through a mailbox full of spam. Others are more sensitive to false positives and would rather deal with unfiltered spam than risk losing mail.
At the ISPs, many of these decisions aren’t made by one person, but the decisions are driven by the business philosophy, requirements and technology. The different consumer ISPs have different philosophies and these show in their spamfiltering.
Gmail, for instance, has a lot of faith in their ability to sort, classify and rank text. This is, after all, what Google does. Therefore, they accept most of the email delivered to Gmail users and then sort after the fact. This fits their technology, their available resources and their business philosophy. They leave as much filtering at the enduser level as they can.
Yahoo, on the other hand, chooses to filter mail at the MTA. While their spamfoldering algorithms are good, they don’t want to waste CPU and filtering effort on mail that they think may be spam. So, they choose to block heavily at the edge, going so far as to rate limit senders that they don’t know about the mail. Endusers are protected from malicious mail and senders have the ability to retry mail until it is accepted.
The same types of entries could be written about Hotmail or AOL. They could even be written about the various spam filter vendors and blocklists. Every company has their own way of doing things and their way reflects their underlying business philosophy.

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