When spam filters fail

Spam filters aren’t perfect. They sometimes catch mail they shouldn’t, although it happens less than some people think. They sometimes fail to catch mail they should.
One of the reason filters fail to catch mail they should is because some spammers invest a lot of time and energy in figuring out how to get past the filters. This is nothing new, 8 or 9 years ago I was in negotiations with a potential client. They told me they had people who started working at 5pm eastern. Their entire job was to craft mail that would get through Hotmail’s filters that day. As soon as they found a particular message that made it to the inbox, they’d blast to their list until the filters caught up. When the filters caught up, they’d start testing again. This went on all night or until the full list was sent.
Since then I’ve heard of a lot of other filter bypass techniques. Some spammers set up thousands of probe accounts at ISPs and would go through and “not spam” their mail to fool the filters (ISPs adapted). Some spammers set up thousands of IPs and rotate through them (ISPs adapted). Some spammers register new domains for every send (ISPs adapted). Some spammers used botnets (ISPs adapted)
I’m sure, even now, there are spammers who are creating new techniques to get through filters. And the ISPs will adapt.

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Email filters

What makes the best email filter? There isn’t really a single answer to that question. Different people and different organizations have different tolerances for how false positives versus false negatives. For instance, we’re quite sensitive to false positives here, so we run extremely conservative filtering and don’t block very much at the MTA level. Other people I know are very sensitive to false negatives and run more aggressive filtering and block quite a bit of mail at the MTA level.
For the major ISPs, the people who plan, approve, design and monitor the filters usually want to maximize customer happiness. They want to deliver as much real mail as possible while blocking as much bad mail. Blocking real mail and letting through bad mail both result in unhappy customers and increase the ISP’s costs, either through customer churn or through support calls. And this is a process, filters are not static. ISPs roll out new filters all the time, sometimes they are an improvement and sometimes they’re not. When they’re not, they’re pulled out of production. This works both for positive filters like Return Path and negative filters like blocklists.
Then there is mail filtering that doesn’t have to do with spam. Business filters, for instance, often block non-business mail. Permission of the recipient often isn’t even a factor. Companies don’t often go out of their way to block personal mail, but if personal mail gets blocked (say the vacation plane ticket or the amazon receipt) they don’t often unblock it. But when you think about why a business provides email, it makes perfect sense. The business provides email to further its own business goals. Some personal usage is usually OK, but if someone notices and blocks personal email then it’s unlikely the business will unblock it, even if the employee opted in.
In the case of email filters, the free market does work. Different ISPs filter mail differently. Some people love Gmail’s filters. Other people think Hotmail has the best filtering. There are different standards for filtering, and that makes email stronger and more robust. Consumers have choices in their mail provider and spamfiltering.

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You can't always get what you want

It’s a problem anyone who has done any delivery work has faced. There’s a client who is having blocklist problems or ISP delivery problems and they won’t pay any attention to what you say. They insist that you talk to the blocklist or the ISP or hand over contacts directly so they can “dialog with” someone internally. They don’t like what they’re hearing, and they hope that the answer will be different if they find a new person to talk to.
The reality is many of the people at ISPs and blocklists don’t want to talk to these types of senders. They may answer a friendly question from someone they know and trust, but sometimes not even then.
Some very large ISPs and major blocklists don’t even take sender questions. They won’t communicate with anyone about any delivery issues.
I’ve had to tell more than a few clients recently that various ISPs and blocklists weren’t interested in helping those clients with their delivery problems. There are two classes of reactions I get from clients. Some clients focus on moving forward. “OK, now what? How can we identify the issue, what data do we have and how can we figure out what the problem is?”
Other clients continue to look for ways to talk to whomever is blocking their mail. They’re convinced if they can just “explain their business model” or be told what they’re doing wrong, that all their delivery problems will magically disappear.
Needless to say those clients who focus on moving forward and looking at the information they do have have much better success resolving their delivery problems. What many senders don’t understand is the wealth of data they have that will help them resolve the issue. And even if they know it’s buried in their files, they don’t always know where to start looking or even what they’re looking for.
But that is, of course, why you hire someone like me who understands spamfiltering and email. I help senders understand how email filters work and identify what parts of their programs are likely to be responsible for delivery issues. I often find the most valuable service I provide to clients is a fresh set of eyes that can see the forest. With my help, they manage to stop obsessing unproductively about one particular symptom and focus on the underlying problems.
Senders who think the holy grail of problem resolution is speaking to the right person at an ISP or blocklist generally are disappointed, even when they hire someone who knows all the right people at the ISPs.  They can’t always get what they want. But I can often help them get what they need.
 
 
 

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Delivery and engagement

Tomorrow is the webinar Mythbusters: Deliverability vs. Engagement. This webinar brings together the ISP speakers from EEC15, plus Matt from Comcast, to expand on their comments. There’s been some confusion about the impact of engagement on delivery and whether or not senders should care about recipient engagement.
My opinion on the matter is well known: recipient engagement drives delivery to the inbox at some providers. I expect tomorrow we’ll hear a couple things from the ISPs.

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