Still with the Microsoft problems

laura
Industry
January 24, 2018

We took a quick trip to Dublin last week. I had every intention of blogging while on the trip, but… oops. I did get to meet with some clients, and had a great dinner while discussing email and delivery.

Coming back, I see a lot of folks still reporting delivery problems to Microsoft properties. I’ve been operating under the assumption this was temporary as kinks were worked out after the migration. I’m still pretty convinced not all of the problems are intentional. Even the best tested code can have issues that only show up under real load with real users. Reading between-some-lines tells me that the tech team is hard at work identifying and fixing issues. There will be changes and things will continue to improve.
With all that being said, I think it’s important to realize that delivering to the new system is not the same as delivering to the old system. This is a major overhaul of their email handling code, representing multiple years worth of planning and development inside Microsoft. It’s very likely that not all of the current delivery problems are the result of deployment. Some of the problems are likely a result of new standards and thresholds for reaching the inbox. What worked a year ago to get into the inbox just doesn’t any more.

What can we do?

The first step is always acceptance.
Accept that …
… the delivery problems aren’t a mistake on Microsoft’s part.
… more difficulty reaching the inbox is not an accident.
… Microsoft may not ever tell us exactly what to do.
In fact, this new round of problems at Microsoft feels a lot like deliverability in the mid-2000s. All we can see is delivery is bad. There is no guidance from postmaster pages or public statements. We’re getting little to no feedback from the ISPs. The support channels seem to be returning messages unrelated to the questions we’ve asked. It’s 2005 delivery all over again!
In many ways we’re luckier now, as we have history and experience to draw on, as well as working relationships with folks inside the ISPs. I have every confidence that the live.com postmaster pages will be updated at some point. Senders will continue testing and figure out how to send mail that makes it to the inbox and that information will get shared through the industry. Microsoft will get to a point where their end is stable and tests give us consistent responses and we can develop meaningful models.
We’re going to have to listen to the ISPs, and not just to what they say on the surface. ISP employees are typically limited to what they can say publicly, but many of them indicate investigative pathways in their responses to questions. As well, there are now trusted intermediaries to disseminate information that will help improve the overall email ecosystem.

It’s not just Microsoft

As I’ve said before, I think we’re going to see changes to more places than Microsoft. AOL addresses are moving to the Yahoo MXs as of February 1, and that opens up a huge number of questions about delivery to AOL. Some of these changes are the result of GDPR, others just a normal service cycle. Whatever the reason, we’re back to having to work out what the black box is hiding. That means we’re going to have to pay attention to what our stats are telling us. More than that, though, we’re going to have to think about what new information we can collect and how to use it to improve delivery.
All in all, deliverability is changing and we’re all going to need to adapt.

The cycle goes on

Monday I published a blog post about the ongoing B2B spam and how annoying it is. I get so many of these they’re becoming an actual problem. 3, 4, 5 a day. And then there’s the ongoing “drip” messages at 4, 6, 8, 12 days. It is getting out of control. It’s spam. It’s annoying. And most of it’s breaking the law.
But, I can also use it as blog (and twitter!) fodder.

It's not fair

In the delivery space, stuff comes in cycles. We’re currently in a cycle where people are unhappy with spam filters. There are two reasons they’re unhappy: false positives and false negatives.
False positives are emails that the user doesn’t think is spam but goes into the bulk folder anyway.
Fales negatives are emails that the user does thing is spam but is delivered to the inbox.
I’ve sat on multiple calls over the course of my career, with clients and potential clients, where the question I cannot answer comes up. “Why do I still get spam?”
I have a lot of thoughts about this question and what it means for a discussion, how it should be answered and what the next steps are. But it’s important to understand that I, and most of my deliverability colleagues, hate this question. Yet we get it all the time. ISPs get it, too.
A big part of the answer is because spammers spend inordinate amounts of time and money trying to figure out how to break filters. In fact, back in 2006 the FTC fined a company almost a million dollars for using deceptive techniques to try and get into filters. One of the things this company did would be to have folks manually create emails to test filters. Once they found a piece of text that would get into the inbox, they’d spam until the filters caught up. Then, they’d start testing content again to see what would get past the filters. Repeat.
This wasn’t some fly by night company. They had beautiful offices in San Francisco with conference rooms overlooking Treasure Island. They were profitable. They were spammers. Of course, not long after the FTC fined them, they filed bankruptcy and disappeared.
Other spammers create and cultivate vast networks of IP addresses and domains to be used in snowshoeing operations. Still other spammers create criminal acts to hijack reputation of legitimate senders to make it to the inbox.
Why do you still get spam? That’s a bit like asking why people speed or run red lights. You still get spam because spammers invest a lot of money and time into sending you spam. They’re OK with only a small percentage of emails getting through filters, they’ll just make it up in volume.
Spam still exists because spammers still exist.

Filters evolving

I started writing this blog post while sitting on a conference call with a bunch of senders discussing some industry wide problems folks are having with delivery. Of course the issue of Microsoft comes up. A lot of senders are struggling with reaching the inbox there and no one has any real, clear guidance on how to resolve it. And the MS employees who regularly answer questions and help folks have been quiet during this time.

In some ways the current situation with Microsoft reminds me of what most deliverability was like a decade ago. Receivers were consistently making changes and they weren’t interacting with senders. There weren’t FBLs really. There weren’t postmaster pages. The reason knowing someone at an ISP was so important was because there was no other way to get information about blocking.
These days, we have a lot more institutional knowledge in the industry. The ISPs realized it was better to invest in infrastructure so senders could resolve issues without having to know the right person. Thus we ended up with postmaster pages and a proliferation of FBLs and best practices and collaboration between senders and receivers and the whole industry benefited.
It is challenging to attempt to troubleshoot deliverability without the benefit of having a contact inside ISPs. But it is absolutely possible. Many ISP folks have moved on over the years; in many cases due to layoffs or having their positions eliminated. The result is ISPs where there often isn’t anyone to talk to about filters.
The lack of contacts doesn’t mean there’s no one there and working. For instance, in the conference call one person asked if we thought Microsoft was going to fix their systems or if this is the new normal. I think both things are actually true. I think Microsoft is discovering all sorts of interesting things about their mail system code now that it’s under full load. I think they’re addressing issues as they come up and as fast as they can. I also think this is some level of a new normal. These are modern filters that implement the lessons learned over the past 20 years of spam filtering without the corresponding cruft.
Overall, I do think we’re in a period of accelerating filter evolution. Address filtering problems has always been a moving target, but we’ve usually been building on known information. Now, we’re kinda starting over. I don’t have a crystal ball and I don’t know exactly what the future will bring. But I think the world of deliverability is going to get challenging again.