Office365/EOP and Outlook.com/Hotmail will converge

Terry Zink posted two informative blog posts recently, the first being the change to unauthenticated mail sent over IPv6 to EOP and the second post about EOP (Office365 and Exchange Hosting) and Outlook.com/Hotmail infrastructure converging.
Exchange Online Protection (EOP) is the filtering system in place for Office 365 and hosted Exchange customers. Outlook.com/Hotmail utilized its own mail filtering system and provides SNDS/JMRP programs.  EOP is setup for redundancy, failover, provides geo-region servers to serve customers, and has supported TLS for over a decade.  Terry explains that Hotmail’s spam filtering technology is more advanced than EOP’s, but EOP’s backend platform is more advanced. The process to convert Outlook.com/Hotmail to use EOP’s filtering system started six months ago and is still a work in progress. Once completed, Outlook.com/Hotmail and Office365/EOP will share the same UX look and feel. The anti-spam technologies will be able to be shared between the two as they will share the same backend infrastructure.
Some of the challenges of merging the two systems include:

  • Outlook.com/Hotmail displays a green shield for senders who are heavily spoofed but authenticate, Outlook Web Access (Office365/EOP) currently does not.
  • Improving backscatter protection so that when a spammer spoofs your email address and the receiving mail server sends an NDR, the NDR does not go to your inbox since you did not send the original message.
  • EOP and Outlook.com/Hotmail both support DMARC, but handles them differently.
  • EOP currently does not send DMARC reports and fixes need to be made to the MTA so that they will be sent.  Outlook.com/Hotmail currently sends DMARC reports.
  • EOP has DKIM-signing on the public road map and once Outlook.com/Hotmail is converted to EOP, they would like to enable DKIM signing for Outlook.com/Hotmail too.

Terry also mentioned that he is non-committal on whether or not Outlook.com/Hotmail will publish a p=reject DMARC report.  He mentioned there are many considerations that must be factored before making a decision but has not ruled out the possibility. In the comments, someone asked about the impact to the SNDS and JMRP programs with the transition of Outlook.com/Hotmail to EOP and Terry says there will be no impact in the near term and they would like to include EOP into Hotmail’s SNDR/JMRP program.

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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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Hotmail moves to SPF authentication

Hotmail has recently stopped using Sender ID for email authentication and switched to authenticating with SPF. The protocol differences between SenderID and SPF were subtle and most senders who were getting a pass at Hotmail were already publishing SPF records.
From an email in my inbox from September:

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