Still with the Microsoft problems

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.