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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More on the attack against Spamhaus and how you can help

While much of the attack against Spamhaus has been mitigated and their services and websites are currently up, the attack is still ongoing.  This is the biggest denial of service attack in history, with as much as 300 gigabits per second hitting Spamhaus servers and their upstream links.
This traffic is so massive, that it’s actually affecting the Internet and web surfers in some parts of the world are seeing network slowdown because of this.
While I know that some of you may be cheering at the idea that Spamhaus is “paying” for their actions, this does not put you on the side of the good. Spamhaus’ actions are legal. The actions of the attackers are clearly illegal. Not only is the attack itself illegal, but many of the sites hosted by the purported source of the attacks provide criminal services.
By cheering for and supporting the attackers, you are supporting criminals.
Anyone who thinks that an appropriate response to a Spamhaus listing is an attack on the very structure of the Internet is one of the bad guys.
You can help, though. This attack is due to open DNS resolvers which are reflecting and amplifying traffic from the attackers. Talk to your IT group. Make sure your resolvers aren’t open and if they are, get them closed. The Open Resolver Project published its list of open resolvers in an effort to shut them down.
Here are some resources for the technical folks.
Open Resolver Project
Closing your resolver by Team Cymru
BCP 38 from the IETF
Ratelimiting DNS
News Articles (some linked above, some coming out after I posted this)
NY Times
BBC News
Cloudflare update
Spamhaus dDOS grows to Internet Threatening Size
Cyber-attack on Spamhaus slows down the internet
Cyberattack on anti-spam group Spamhaus has ripple effects
Biggest DDoS Attack Ever Hits Internet
Spamhaus accuses Cyberbunker of massive cyberattack

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Content, trigger words and subject lines

There’s been quite a bit of traffic on twitter this afternoon about a recent blog post by Hubspot identifying trigger words senders should avoid in an email subject line. A number of email experts are assuring the world that content doesn’t matter and are arguing on twitter and in the post comments that no one will block an email because those words are in the subject line.
As usually, I think everyone else is a little bit right and a little bit wrong.
The words and phrases posted by Hubspot are pulled out of the Spamassassin rule set. Using those words or exact phrases will cause a spam score to go up, sometimes by a little (0.5 points) and sometimes by a lot (3+ points). Most spamassassin installations consider anything with more than 5 points to be spam so a 3 point score for a subject line may cause mail to be filtered.
The folks who are outraged at the blog post, though, don’t seem to have read the article very closely. Hubspot doesn’t actually say that using trigger words will get mail blocked. What they say is a lot more reasonable than that.

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Mail that looks good on desktop and mobile

Over the weekend I noticed a new CSS framework aimed at email rather than web development, “Antwort“.
This isn’t the first or only framework for email content, but this one looks simple and robust, and it allows for content that doesn’t just adapt for different sized displays but looks good on all of them. The idea behind it is to divide your content into columns, magazine style, then display the columns side-by-side on desktop clients and top to bottom on mobile clients. That opens up much more interesting designs than the more common single fluid column approach.

It looks nice, it supports pretty much every interesting email client, but it also comes with some directions based on real world experience.

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