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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March 2016: The Month In Email

Happy April! I’m just back from the EEC conference in New Orleans, which was terrific. I wrote a quick post about a great session on content marketing, and I’ll have more to add about the rest of the conference over the next week or so. Stay tuned!
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Here’s a look at what caught our attention in March:
On the DMARC front, we noted that both Yahoo and mail.ru are moving forward with p=reject, and Steve offered some advice for ESPs and software developers on methods for handling this gracefully. I also answered an Ask Laura question about making the decision to publish DMARC. Look for more on that in this month’s Ask Laura questions…
Our other Ask Laura question this month was about changing ESPs, which senders do for many reasons. It’s useful to know that there will generally be some shifts in deliverability with any move. Different ESPs measure engagement in different ways, and other issues may arise in the transition, so it’s good to be aware of these if you’re contemplating a change.
In industry news, I wrote a sort of meta-post about how the Internet is hard (related: where do you stand on the great Internet vs. internet debate? Comment below!) and we saw several examples of that this month, including a privacy debacle at Florida State University. Marketing is hard, too. I revisited an old post about a fraud case where a woman sued Toyota over an email marketing “prank”. As always, my best practices recommendation for these sorts of things (and everything else!) really boils down to one thing: send wanted email.
Steve wrote extensively about SPF this month in two must-read posts, where he explained the SPF rule of ten and how to optimize your SPF records. He also wrote about Mutt, the much-loved command line email client, and marked the passing of industry pioneer Ray Tomlinson, who, in addition to his many accomplishments, was by all accounts a very thoughtful and generous man.
Finally, I occasionally like to take a moment and follow the twisty paths that lead to my spam folder. Here’s a look at how Ugg spams my email doppelganger, MRS LAURA CORBISHLEY. In other spam news, there’s a lot of very interesting data in the recent 10 Worst list from Spamhaus. Take a look if you haven’t seen it yet.

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Return Path on Content Filtering

Return Path have an interesting post up about content filtering. I like the model of 3 different kinds of filters, in fact it’s one I’ve been using with clients for over 18 months. Spamfiltering isn’t really about one number or one filter result, it’s a complex interaction of lots of different heuristics designed to answer the question: do recipients want this kind of mail?

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