List-Unsub header

Benjamin asked in the comments where in the interface the “unsubscribe” or “block” popup appeared. This is the dialog box Microsoft uses when the add the “unsubscribe here” link at the top of a message. Screenshots taken today from my Hotmail account:
At this point we have 3 of the major webmail providers (Yahoo, Microsoft, Gmail) using List-Unsubscribe headers and at least one mobile client (Apple Mail). 20 years on it seems List-Unsubscribe is finally gaining traction.
Notice, too, that ISPs hold their own mail to the same standards as outside mail. This really is Microsoft offering to let me block everything from MSN News.
 

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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.
 

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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.

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