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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April 2015: The Month in Email

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Email predictions for 2015

Welcome to a whole new year. It seems the changing of the year brings out people predicting what they think will happen in the coming year. It’s something I’ve indulged in a couple times over my years of blogging, but email is a generally stable technology and it’s kind of boring to predict a new interface or a minor tweak to filters. Of course, many bloggers will go way out on a limb and predict the death of email, but I think that’s been way over done.
ChangeConstant
Even major technical advancements, like authentication protocols and the rise of IPv6, are not usually sudden. They’re discussed and refined through the IETF process. While some of these changes may seem “all of a sudden” to some end users, they’re usually the result of years of work from dedicated volunteers. The internet really doesn’t do flag days.
One major change in 2014, that had significant implications for email as a whole, was a free mail provider abruptly publishing a DMARC p=reject policy. This caused a lot of issues for some small business senders and for many individual users. Mailing list maintainers are still dealing with some of the fallout, and there are ongoing discussions about how best to mitigate the problems DMARC causes non-commercial email.
Still, DMARC as a protocol has been in development for a few years. A number of large brands and commercial organizations were publishing p=reject policies. The big mail providers were implementing DMARC checking, and rejection, on their inbound mail. In fact, this rollout is one of the reasons that the publishing of p=reject was a problem. With the flip of a switch, mail that was once deliverable became undeliverable.
Looking back through any of the 2014 predictions, I don’t think anyone predicted that two major mailbox providers would implement p=reject policies, causing widespread delivery failures across the Internet. I certainly wouldn’t have predicted it, all of my discussions with people about DMARC centered around business using DMARC to protect their brand. No one mentioned ISPs using it to force their customers away from 3rd party services and discussion lists.
I think the only constant in the world of email is change, and most of the time that change isn’t that massive or sudden, 2014 and the DMARC upheaval notwithstanding.
But, still, I have some thoughts on what might happen in the coming year. Mostly more of the same as we’ve seen over the last few years. But there are a couple areas I think we’ll see some progress made.

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Office365/EOP IPv6 changes starting today

Terry Zink at Microsoft posted earlier this week that Office365/Exchange Online Protection will have a significant change this week. Office365 uses Exchange Online Protection (EOP) for spam filtering and email protection. One of the requirements to send to EOP over IPv6 is to have the email authenticated with either SPF or DKIM.  If the mail sent to Office365/EOP over IPv6 is not authenticated with SPF or DKIM, EOP would reject the message with a 554 hard bounce message.  Most mail servers accept the 554 status code and would not retry the message.  After multiple 5xx hard bounces to an email address, many mail servers would unsubscribe the user from future email campaigns.  The update starting today April 24, will change the error status code for unauthenticated mail to EOP from a 554 hard bounce to a 450 soft bounce and a RFC-compliant and properly configured mail server would then retry the message.
Prior to April 24, 2015, EOP responds to unauthenticated mail with a status code of: “554 5.7.26 Service Unavailable, message sent over IPv6 must pass either SPF or DKIM validation”.

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SNDS is back

For years now, Microsoft has maintained Smart Network Data Services (SNDS) for anyone sending mail to Hotmail/Outlook/Live.com. This is a great way for anyone responsible for an IP sending mail to hotmail to monitor what traffic Hotmail is seeing from that IP address.
This morning I got up to a number of people complaining that logins were failing on the website and the API was down. I contacted the person behind SNDS and they confirmed there was a problem and they were fixing it.
Sometime this afternoon it was possible to login to the SNDS interface again, so it looks like they did fix it.
A bit of a warning, though, don’t expect to see any of the data from the last few days. There seems to be something with SNDS that means that when the service is down data isn’t collected or available. In the past when there have been problems, older data was not populated when the service came back.

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