We are unable to send email to Microsoft services (like Outlook and Hotmail)

I mentioned in the year-end reflection post that I’ve been dealing with several serious tech issues for the last few months. Well, this is about one of the most frustrating ones.

In the last few months we have had multiple issues with major email services rejecting emails sent from canandianatheist.com. For example, at one point this past December Gmail was refusing our emails; turned out to be something broke internally in their quota system. Thankfully they eventually fixed it.

However, starting a few months back, emails sent from canandianatheist.com to addresses on Microsoft email services—this includes Outlook and Hotmail, as well as live.com, msn.com, and probably others—started getting bounced. The error messages said that we were on a block list.

Discovering we’re on a block list is not an uncommon occurrence, because people frequently report Canadian Atheist for spam and other violations. We don’t spam, but they still report us. I wouldn’t be surprised if some of them were ideologically motivated, but sometimes they’re just dumb and lazy: they signed up for email updates from CA, then later decided they didn’t want them, but rather than use the unsubscribe link that is in every email, they just say we’re spamming them.

As I said, this is just the way things work, so part of my job is making sure we get removed from these block lists. (As an aside, this continued headache is why I’m thinking of removing email subscriptions. I haven’t committed to this plan yet, but frankly, there are so many other ways you can follow Canadian Atheist, that I don’t think email subscriptions are worth the hassle.)

Now Microsoft’s email services, to my knowledge, use Spamhaus for their email protection. This shouldn’t be a problem, because both our IP and domain are in good standing: Canadian Atheist has never spammed.

However, it turns out that Microsoft’s email services are doing something a little more nefarious. They apparently also have their own private, internal block list. And the evidence—collected by multiple internet service providers—seems to be that they’re blocking entire networks. In other words, they’re not just blocking 172.93.123.116 (Canadian Atheist’s current IP), they’re probably blocking all IPs from 172.93.123.0 to 172.93.123.255 inclusive. Or, possibly, everything starting with 172.93.

So how does one fix this problem?

Well, turns out, one has to grovel to Microsoft to stop blocking half the fucking Internet (amusingly, they seem to have even blocked their own Azure services)… which sounds like a small price to pay to be able to send email to the many, many people who use Microsoft’s services, but there’s a catch. Turns out that when you block half the Internet, you end up with a lot of people asking you to consider unblocking them. A responsible service provider would have enough people on staff to handle those requests… but Microsoft apparently doesn’t. So everyone’s mitigation requests are simply being denied. (At least at first. Apparently if you persist you do eventually get through; though I haven’t gotten that far yet. I’ve also heard rumours that you can actually get heard if you sign up for Microsoft’s Smart Network Data Services. Yeah, no, not happening.)

So, the upshot of this is that unless and until Microsoft fixes this issue, no emails from canadianatheist.com can reach email addresses at Outlook or Hotmail (or any other Microsoft-controlled address). There is nothing we can do to fix this; this is a Microsoft-internal problem. I’m going to presume it isn’t a planned shakedown to get us to buy into their services, and is just incompetence on their part. But it doesn’t matter either way, because we can’t fix this, they have to, and it’s not likely that they’ll care enough to do so. They’ve let the problem fester for months, after all.

So what does that mean for you? Well, if you’re using one of Microsoft’s email services, and you actually want to receive Canadian Atheist emails… you either need to contact your hosting provider—Microsoft—and kindly request they fix the problem… or you need to get a better email provider, because, let’s be honest, Microsoft’s free email services have never been all that great, and without Gmail forcing them to up their game, their services would probably be unusable today. Maybe check out Proton mail.