IP reputation and email delivery

IP reputation is a measure of how much wanted mail a particular IP address sends.  This wanted mail is measured as a portion of the total email sent from that IP. Initially IP reputation was really the be all and end all of reputation, there was no real good way to authenticate a domain or a from address. Many ISPs built complex IP reputation models to evaluate mail based on the IP that sent the mail.
These IP reputation models were the best we had, but there were a lot of ways for spammers to game the system. Some spammers would create lots of accounts at ISPs and use them to open and interact with mail. Other spammers would trickle their mail out over hundreds or thousands of IPs in the hopes of diluting the badness enough to get to the inbox. Through it all they kept trying to get mail out through reputable ESPs, either by posing as legitimate customers or compromising servers.
These things worked for a while, but the ISPs started looking harder at the recipient pool in order to figure out if the interactions were real or not. They started looking at the total amount of identical mail coming from multiple IP addresses. The ISPs couldn’t rely on IP reputation so they started to dig down and get into content based filtering.
As the ISPs got better at identifying content and filtering on factors other than source IP, the importance of the IP address on inbox delivery changed. No longer was it good enough to have a high reputation IP sending mail.
These days your IP reputation dictates how fast you can send mail to a particular ISP. But a high reputation IP isn’t sufficient to get all the mail in the inbox. It’s really content that drives the inbox / bulk folder decisions these days.
 
Generally IPs that the ISP has not seen email traffic from before start out with a slight negative reputation. This is because most new IPs are actually infected machines. The negative reputation translates to rate limiting. The rate limiting minimizes people getting spam while the ISP works out if this is a real sender or a spammer.
Some ISPs put mail in the inbox and bulk foldering during the whitelisting process. In this case what they’re doing is seeing if your recipients care enough about your mail to look for it in the bulk folder. If they do, and they mark the mail as “not spam” then this feeds back to the sender reputation and the IP reputation.
If you’re seeing a lot of bulk foldering of mail, it’s unlikely there’s anything IP reputation based to do. Instead of worrying about IP reputation, focus instead on the content of the mail and see what you may need to do to improve the reputation of the domains and URLs (or landing pages) in the emails.

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ISPs speak at M3AAWG

Last week at M3AAWG representatives from AOL, Yahoo, Gmail and Outlook spoke about their anti-spam technologies and what the organizations were looking for in email.
This session was question and answers, with the moderator asking the majority of the questions. These answers are paraphrased from my notes or the MAAWG twitter stream from the session.
What are your biggest frustrations?
AOL: When senders complain they can’t get mail in and we go look at their stats and complaints are high. Users just don’t love that mail. If complaints are high look at what you may have done differently, content does have an effect on complaints.
Outlook: When we tightened down filters 8 years ago we had to do it. Half of the mail in our users inbox was spam and we were losing a steady number of customers. The filter changes disrupted a lot of senders and caused a lot of pain. But these days only 0.5% of mail in the inbox is spam.  Things happen so fast, though, that the stress can frustrate the team.
Gmail: Good senders do email badly sometimes and their mail gets bulked. Senders have to get the basic email hygiene practices right. Love your users and they’ll love you back.
What’s your philosophy and approach towards mail?
AOL: There is a balance that needs to be struck between good and bad mail. The postmaster team reminds the blocking team that not all mail is bad or malicious. They are the sender advocates inside AOL. But the blocking team deals with so much bad mail, they sometimes forget that some mail is good.
Yahoo: User experience. The user always comes first. We strive to protect them from malicious mail and provide them with the emails they want to see. Everything else is secondary.
Gmail: The faster we stop spam the less spam that gets sent overall. We have highly adaptive filters that can react extremely quickly to spam. This frustrates the spammers and they will give up.
Outlook: The core customer is the mailbox user and they are a priority. We think we have most of the hardcore spam under control, and now we’re focused on personalizing the inbox for each user. Everyone online should hold partners accountable and they should expect to be held accountable in turn. This isn’t just a sender / ESP thing, ISPs block each other if there are spam problems.
What are some of your most outrageous requests?
We’ve been threatened with lawsuits because senders just don’t want to do the work to fix things. Some senders try to extort us. Other senders go to the advertising execs and get the execs to yell at the filtering team.
Coming to MAAWG and getting cornered to talk about a particular sender problem. Some senders have even offered money just to get mail to the spam folder.
Senders who escalate through the wrong channels. We spent all this money and time creating channels where you can contact us, and then senders don’t use them.
Confusing business interests with product interests. These are separate things and we can’t change the product to match your business interest.
What are your recommendations for changing behaviors?
Outlook: We provide lots of tools to let you see what your recipients are doing. USE THE TOOLS. Pay attention to your recipient interaction with mail. Re-opt-in recipients periodically. Think about that mail that is never opened. Monitor how people interact with your mail. When you have a problem, use our webpages and our forms. Standard delivery problems have a play book. We’re going to follow that playbook and if you try to get personal attention it’s going to slow things down. If there’s a process problem, we are reachable and can handle them personally. But use the postmaster page for most things.
Gmail: Get your hygiene right. If you get your hygiene right, deliverability just works. If you’re seeing blocking, that’s because users are marking your mail as spam. Pay attention to what the major receivers publish on their postmaster pages. Don’t just follow the letter of the law, follow the spirit as well. Our responsibility, as an ISP, is to detect spam and not spam. Good mailers make that harder on us because they do thinks that look like spammers. This doesn’t get spammer mail in more, it gets legitimate mail in less. Use a real opt-in system, don’t just rely on an implied opt-in because someone made a purchase or something.
Yahoo: ESPs are pretty good about screening their customers, so pay attention to what your ESPs are saying. Send mail people want. Verify that the email addresses given to you actually belong to people who want your mail. Have better sender practices.
What do you think about seed accounts?
The panel wasn’t very happy about the use of seed accounts. Seeds are not that useful any longer, as the ISPs move to more and more personalized delivery. Too much time and too many cycles are used debugging seed accounts. The dynamic delivery works all ways.
When things go wrong what should we do?
AOL: Open a ticket. We know we’ve been lax recently, but have worked out of our backlog and are caught up to date. Using the ticketing system also justifies us getting more headcount and makes everyone’s experience better. Also, don’t continue what you’re doing. Pausing sending while you’re troubleshooting the issue. We won’t adjust a rep for you, but we may be able to help you.
Gmail: Do not jump the gun and open a ticket on the first mail to the spam folder. Our filters are so dynamic, they update every few minutes in some cases. Be sure there is a problem. If you are sure you’re following the spirit and letter of the sender guidelines you can submit a ticket. We don’t respond to tickets, but we work every single one. When you’re opening a ticket provide complete information and full headers, and use the headers from your own email address not headers from a seed account. Give us a clear and concise description of the problem. Also, use the gmail product forum, it is monitored by employees and it’s our preferred way of getting information to the anti-abuse team. Common issues lots of senders are having will get addressed faster.
Outlook: Dig in and do your own troubleshooting, don’t rely on us to tell you what to fix. The support teams don’t have a lot of resources so use our public information. If you make our job harder, then it takes longer to get things done. But tell us what changes you’ve made. If you’ve fixed something, and tell us, our process is different than if you’re just asking for a delisting or asking for information. When you’ve fixed things we will respond faster.
How fast should users expect filters to respond after making changes?
Filters update continually so they should start seeing delivery changes almost immediately. What we find is people tell us they’ve made changes, but they haven’t made enough or made the right ones. If the filters don’t update, then you’ve not fixed the problem.

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April: The month in email

April was a big month of changes in the email world, and here at Word to the Wise as we launched our new site, blog and logo.
DMARC
The big story this month has been DMARC, which started with a policy change Yahoo made on April 4 updating their DMARC policy from “report” to “reject”. We began our coverage with a brief DMARC primer to explain the basics around these policy statements and why senders are moving in this direction. We shared some example bounces due to Yahoo’s p=reject, and talked about how to fix discussion lists to work with the new Yahoo policy. We gathered some pointers to other articles worth reading on the Yahoo DMARC situation, and suggested some options for dealing with DMARC for mail intermediaries. Yahoo issued a statement about this on April 11th, explaining that it had been highly effective in reducing spoofed email. We also noted a great writeup on the situation from Christine at ReturnPath. On April 22nd, AOL also announced a DMARC p=reject record.  We talked a bit about who might be next (Gmail?) and discussed how Comcast chose to implement DMARC policies, using p=reject not for user email, but only for the domains they use to communicate directly with customers. We expect to see more discussion and policy changes over the next few weeks, so stay tuned.
Spamtraps
We wrote three posts in our continuing discussion about spamtraps. The first was in response to a webinar from the DMA and EEC, where we talked about how different kinds of traps are used in different ways, and, again, how spamtraps are just a symptom of a larger problem. Following that, we wrote more about some ongoing debate on traps as we continued to point out that each trap represents a lost opportunity for marketers to connect with customers, which is really where we hope email program managers will focus. And finally, we tried to put some myths about typo traps to rest. As I mentioned in that last post, I feel like I’m repeating myself over and over again, but I want to make sure that people get good information about how these tools are used and misused.
Security
We started the month by saying “Security has to become a bigger priority for companies” and indeed, the internet continued to see security breaches in April, including the very serious Heartbleed vulnerability in SSL. In the email world, AOL experienced a compromise, which contributed to some of the DMARC policy changes we discussed above. In a followup post, we talked about how these breaches appear to be escalating. Again, we expect to hear more about this in the next weeks and months.
Best Practices
Ending on a positive note, we had a few posts about best practices and some email basics. We started with a pointer to Al Iverson’s post on masking whois info and why not to do it. Steve wrote up a comprehensive post with everything you ever wanted to know about the From header and RFC5322. I talked about how companies ignore opt-outs, and why they shouldn’t. I shared a really good example of a third-party email message, and also talked about message volume. And finally, we talked about how and why we warm up IP addresses.
Let us know if there’s anything you’d like to hear more about in May!

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Welcome to our new site

We’re very excited and pleased to launch our redesigned website and blog.
As you can see, we have a new logo and an official color scheme. In addition to the cosmetic changes, we’ve improved the underlying structure. We have pages dedicted to our offerings, including Abacus and information about our consulting services.
We’ve also consolidated a lot of the information spread across different website. The ISP Information page is updated and current (finally! all the Goodmail references are gone). And the ISP specific pages are here instead of over on the wiki.
Two features we’re quite excited about are our wiseWords and wiseTools.
wiseWords is our place to publish more in depth articles about email, delivery and the Internet than the blog. Over time, I expect this to grow to encompas a full email knowledge base. We’ve also published some white papers for download.
wiseTools is the umbrella for our useful email tools, including the tools published at emailstuff.org. They’re still at emailstuff.org, but they’re also here at tools.wordtothewise.com.
We’ve done our best to make sure links transfer from the old site to the new one, but feel free to contact us if you find a broken link.
You may find your first comment on the new blog goes into moderation the first time you post. But once you’ve been approved, comments won’t go through moderation a second time.
Our new website is just the first of many new things we are hoping to roll out in the coming months.

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