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:

SMTP error from remote mail server after end of data:
521 5.2.1 : AOL will not accept delivery of this message.

Mike also mentioned his IP reputation is good, when he checks at AOL so he doesn’t understand why mail is being blocked.
I think the big clue is after the end of data and would look at the full content of the mail, particularly domains and URLs, to identify is triggering the block.
In the SMTP transaction there are only a few places the ISP can stop the transaction and each spot tells us different things about why the ISP is rejecting the message.

After connection

A block after connection is a block either against the IP address or against the domain in the rDNS of the IP. IPs with no rDNS or generic DNS can also be blocked here. Blocks here do happen, but many recipients will let the SMTP transaction continue.

After HELO/EHLO

A block after HELO/EHLO is often a block against the domain in the HELO/EHLO or against a particular HELO/EHLO. Malware and bots often have distinctive HELO/EHLO patterns and it’s common for those kinds of senders to be blocked at this point.

After Mail From

A block after Mail From is often directed at the domain in the bounce string. Some senders do check to make sure the domain has a MX and will block if it doesn’t. Blocks don’t happen here very often.

After RCPT To

Blocks here are not always spam related. Most of the delivery failures at this point have to do with non-existent addresses.

After DATA

Blocks after data mean the ISP has actually seen the full content of the email. If a block comes after DATA the full content of the message including the recipient and their permission status should be evaluated as part of the determination about what is triggering the block.
Using when the rejection happened is an important part of understanding why a block happened. For instance, if a block happens before DATA, you know that content isn’t relevant, because the ISP never saw the content. If a block happened before Mail From: you know it’s the IP address reputation or configuration. If a block happened after DATA you know you need to look at the whole message.
 

DOD breaks links in .mil clients
Thoughts on SenderScore

Related Posts

Pattern matching primates

Why do we see faces where there are none? Paradolia
Why do we look at random noise and see patterns? Patternicity
Why do we think we have discovered what’s causing filtering if we change one thing and email gets through?
It’s all because we’re pattern matching primates, or as Michael Shermer puts it “people believe weird things because of our evolved need to believe nonweird things.”
Our brains are amazing and complex and filter a lot of information so we don’t have to think of it. Our brains also fill in a lot of holes. We’re primed at seeing patterns, even when there’s no real pattern. Our brains can, and do, lie to us all the time. For me, some of the important part of my Ph.D. work was learning to NOT trust what I thought I saw, and rather to effectively observe and test. Testing means setting up experiments in different ways to make it easier to not draw false conclusions.
Humans are also prone to confirmation bias: where we assign more weight to things that agree with our preconceived notions.
Take the email marketer who makes a number of changes to a campaign. They change some of the recipient targeting, they add in a couple URLs, they restructure the mail to change the text to image ratio and they add the word free to the subject line. The mail gets filtered to the bulk folder and they immediately jump to the word free as the proximate cause of the filtering. They changed a lot of things but they focus on the word free. 
Then they remove the word free from the subject line and all of a sudden the emails are delivering. Clearly the filter in question is blocking mail with free in the subject line.
Well, no. Not really. Filters are bigger and more complex than any of us can really understand. I remember a couple years ago, when a few of my close friends were working at AOL on their filter team. A couple times they related stories where the filters were doing things that not even the developers really understood.
That was a good 5 or 6 years ago, and filters have only gotten more complex and more autonomous. Google uses an artificial neural network as their spam filter.  I don’t really believe that anything this complex just looks at free in the subject line and filters based on that.
It may be that one thing used to be responsible for filtering, but those days are long gone. Modern email filters evaluate dozens or hundreds of factors. There’s rarely one thing that causes mail to go to the bulk folder. So many variables are evaluated by filters that there’s really no way to pinpoint the EXACT thing that caused a filter to trigger. In fact, it’s usually not one thing. It could be any number of things all adding up to mean this may not be mail that should go to the inbox.
There are, of course, some filters that are one factor. Filters that listen to p=reject requests can and do discard mail that fails authentication. Virus filters will often discard mail if they detect a virus in the mail. Filters that use blocklists will discard mail simply due to a listing on the blocklist.
Those filters address the easy mail. They leave the hard decisions to the more complex filters. Most of those filters are a lot more accurate than we are at matching patterns. Us pattern matching primates want to see patterns and so we find them.
 

Read More

Reputation is about behavior

meter19
Reputation is calculated based on actions. Send mail people want and like and interact with and get a good reputation. Send mail people don’t want and don’t like and don’t interact with and get a bad reputation.
 
Reputation is not
… about who the sender is.
… about legitimacy.
… about speech.
… about message.
Reputation is
… about sender behavior.
… about recipient behavior.
… about how wanted a particular mail is forecast to be.
… based on facts.
Reputation isn’t really that complicated, but there are a lot of different beliefs about reputation that seem to make it complicated.
The reputation of a sender can be different at different receivers.
Senders sometimes target domains differently. That means one receiver may see acceptable behavior but another receiver may see a completely different behavior.  
Receivers sometimes have different standards. These include standards for what bad behavior is and how it is measured. They may also have different thresholds for things like complaints and bounces.
What this means is that delivery at one receiver has no impact on delivery at another. Just because ISP A delivers a particular mail to the inbox doesn’t mean that ISP B will accept the same mail. Each receiver has their own standards and sometimes senders need to tune mail for a specific receiver. One of my clients, for instance, tunes engagement filters based on the webmail domain in the email address. Webmail domain A needs a different level of engagement than webmail domain B.
Public reputation measures are based on data feeds.
There are multiple public sources where senders can check their reputation. Most of these sources depend on data feeds from receiver partners. Sometimes they curate and maintain their own data sources, often in the form of spamtrap feeds. But these public sources are only as good as their data analysis. Sometimes, they can show a good reputation where there isn’t one, or a bad reputation where there isn’t one.
Email reputation is composed of lots of different reputations. 
Email reputation determines delivery.  Getting to the inbox doesn’t mean sending from an IP with a good reputation. IP reputation is combined with domain reputation and content reputation to get the email reputation. IP reputation is often treated as the only valuable reputation because of the prevalence of IP based blocking. But there are SMTP level blocks against domains as well, often for phishing or virus links. Good IP reputation is necessary but not sufficient for good email delivery.
Reputation is about what a sender does, not about who a sender is.
Just because a company is a household name doesn’t mean their practices are good enough to make it to the inbox. Email is a meritocracy. Send mail that merits the inbox and it will get to recipients. Send email that doesn’t, and suffer the repercussions.

Read More

Confusing the engineers

We went camping last weekend with a bunch of friends. Had a great time relaxing on the banks of the Tuolumne River, eating way too much and visiting.
On Saturday I was wearing a somewhat geeky t-shirt. It said 554: abort mission. (Thank you MessageSystems). At some point on Saturday every engineer came up to me, read my shirt and then looked at me and said “That’s not HTTP.”
That lead to various discussions about how their junior engineers don’t actually know SMTP at all. Why? Because the SMTP libraries just work. Apparently the HTTP libraries aren’t that great, so folks have to learn more about HTTP to troubleshoot and use them.
I’m sure there’s a joke in there somewhere: A Kindle engineer, an Android engineer and a robot engineer walk into a campsite…
EmailFilters_boxes_forblogIt did leave me thinking, though, about how it’s not that easy to run your own mail server these days. Gone are the days when running your own server was cost effective and easy. These days, there is just too much spam coming in. Crafting filters is a skilled job. It’s not that hard to run good filters. But to run good filters takes time to do well.
There are also a lot of challenges to sending mail. One of the discussions I had at the campsite was how hard it was to configure outbound mail. The engineer was helping a friend set up a website and trying to get the website to send notifications to the friend. But without setting up authentication the mail kept silently failing.
Of course, we do run our own mail server. But it’s our job and, in many ways, it keeps us honest. We don’t run many filters meaning we see what spammers are doing and can use our own experiences to better understand what commercial filters are dealing with.
For most people, though, I really think using a service is the right solution. Find one with filters that meet your needs and just pay them to deal with the headache.
 

Read More