Are you blocking yourself?

One thing that catches me up with clients sometimes is their own spam filters block their own content. It happens. In some cases the client is using an appliance. The client’s reputation is bad enough that the appliance actually blocks mail. Often these clients have no idea they are blocking their own mail, until we try and send them something and the mail is rejected.
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Typically, the issue is their domains are the problem. We mention the domains in email, and the filters do what filters do. We work around this by abbreviating the domains or calling, it’s not a big deal.
It’s a great demonstration of content filters, though. The content (the client’s domain) is blocked even when it comes from an IP with a good reputation. In fact, with Gmail I can often tell “how bad” a domain reputation is. Most mail I send from WttW to my gmail address goes to the inbox, even when the client is reporting bulk foldering at Gmail. But every once in a while a domain has such a bad reputation that any mail mentioning that domain goes to bulk.
Most folks in the deliverability space know the big players in the filtering market: Barracuda, Cloudmark, ProofPoint, etc. Those same people have no idea what filters their company uses and have never even really thought about it.
Do you know what filter your company is using to protect employees from spam?
 
 
 

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The death of IP based reputation

Back in the dark ages of email delivery the only thing that really mattered to get your email into the inbox was having a good IP reputation. If your IP sent good mail most of the time, then that mail got into the inbox and all was well with the world. All that mattered was that good IP reputation. Even better for the people who wanted to game the system and get their spam into the inbox, there were many ways to get around IP reputation.
Every time the ISPs and spam filtering companies would work out a way to block spam using IP addresses, spammers would figure out a way around the problem. ISPs started blocking IPs so spammers moved to open relays. Filters started blocking open relays, so spammers moved to open proxies. Filters started blocking mail open proxies so spammers created botnets. Filters started blocking botnets, so spammers started stealing IP reputation by compromising ESP and ISP user accounts.  Filters were constantly playing catchup with the next new method of getting a good IP reputation, while still sending spam.
While spammers were adapting and subverting IP based filtering a number of other things were happening. Many smart people in the email space were looking at improving authentication technology. SPF was the beginning, but problems with SPF led to Domains Keys and DKIM. Now we’re even seeing protocols (DMARC) layered on top of DKIM. Additionally, the price of data storage and processing got cheaper and data mining software got better.
The improvement in processing power, data mining and data storage made it actually feasible for ISPs and filtering companies to analyze content at standard email delivery speeds. Since all IPv4 addresses are now allocated, most companies are planning for mail services to migrate to IPv6. There are too many IPv6 IPss to rely on IP reputation for delivery decisions.
What this means is that in the modern email filtering system, IPs are only a portion of the information filters look at when making delivery decisions. Now, filters look at the overall content of the email, including images and URLs. Many filters are even following URLs to confirm the landing pages aren’t hosting malicious software, or isn’t content that’s been blocked before. Some filters are looking at DNS entries like nameservers and seeing if those nameservers are associated with bad mail. That’s even before we get to the user feedback, in the form of “this is spam” or “this is not spam” clicks, which now seem to affect both content, domain and IP reputation.
I don’t expect IP reputation to become a complete non-issue. I think it’s still valuable data for ISPs and filters to evaluate as part of the delivery decision process. That being said, IP reputation is so much less a guiding factor in good email delivery than it was 3 or 4 years ago. Just having an IP with a great reputation is not sufficient for inbox delivery. You have to have a good IP reputation and good content and good URLs.
Anyone who wants good email delivery should consider their IP reputation, but only as one piece of the delivery strategy. Focusing on a great IP reputation will not guarantee good inbox delivery. Look at the whole program, not just a small part of it.

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Thoughts from #EEC16

EEC16 was my first Email Experience conference. I was very impressed. Dennis, Len, and Ryan put together a great program. I made it to two of the keynotes and both took me out of an email focused place to look at the bigger picture.
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Patrick Scissons discussed his experiences creating marketing and advertising campaigns for good and to share messages. Some of the campaigns were ones I’d seen as a consumer, or on the news. One of the campaigns he talked about specifically was for the group Moms Demand Action, looking at sensible gun control in the US. The images and symbology used in those campaigns were striking and very effective.
Kelly McEvers talked about her experiences as a correspondent in the middle east during the Arab Spring. She is an engaging speaker, as one who does radio should be. Her overall message and theme was that sometimes events are such that you need to throw the list away and go with it. As someone who lives by “the list” and tries to make sure I’m prepared for every eventuality I found that a very useful message. Particularly when throwing away “the list” turned into some massively successful stories.
In terms of sessions, I found the email content session fascinating. I blogged about content in email last week and did some live tweeting, too. What really hit me after that session was that good marketing drives deliverability. Everything that Carey Kegel was talking about in terms of better marketing, sounded like things I recommend to clients to drive deliverability.
Back in 2012 I was writing posts about how delivery and marketing were somewhat at odds with each other. The premise was that marketing was about creating mindshare, and repeating a message so often a recipient couldn’t forget it. In email, repetition can cause recipient fatigue and drive delivery problems. But what I’m hearing now, from the leading minds of email marketers, is that email marketing works better if you send relevant and useful information to consumers. Recipients are key and you can’t just keep hammering them, you have to provide them with some value.
It seems marketing has finally come around to the delivery point of view.
 
 

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Dodging filters makes for effective spamming

Spam is still 80 – 90% of global email volume, depending on which study look at. Most of that spam doesn’t make it to the inbox; ISPs reject a lot of it during the SMTP transaction and put much of rest of it in the bulk folder. But as the volumes of spam have grown, ISPs and filters are relying more and more on automation. Gone are the days when a team of people could manually review spam and tune filters. There’s just too much of it out there for it to be cost effective to manually review filters.
In some ways, though, automatic filters are easier to avoid than manual filters. Take a spam that I received at multiple addresses today. It’s an advertisement for lists to “meet my marketing needs.” I started out looking at this mail to walk readers through all of the reasons I distrusted this mail. But some testing, the same sorts of testing I do for client mails, told me that this mail was making it to the inbox at major ISPs.
What told me this mail was spam? Let’s look at the evidence.
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