Microsoft's SmartScreen: Embrace, Extend, and Extinguish for Email
Never one to learn from their mistakes, Microsoft is using their email services (as I recently discovered after receiving a message from a relative who was still using an old Hotmail address) as a platform for "innovations" that attack standard services once again:
IPs not previously used to send email typically don't have any reputation built up in our systems. As a result, emails from new IPs are more likely to experience deliverability issues. Once the IP has built a reputation for not sending spam, Outlook.com will typically allow for a better email delivery experience.Read that over a couple times and, if it makes sense to you, you might just be dumb enough to work for Microsoft. Let me rephrase it without the industry jargon so that you'll be overqualified for the job:
If you don't send much email, we're too idiotic to figure out that you're obviously not spamming. So we're not going to deliver any of your messages until we've delivered enough of your messages.
Yes, that's some top-shelf broken logic you're working with, Microsoft. A presumption of guilt and a refusal to even reverse the burden of proof! I sent them a support request asking them how they expect email to function:
The specific problem I’m having is that you are giving Microsoft users a false sense of deliverability when you send messages to servers you do not accept messages from. If you do not fix this issue, the only resolution I can think of is to block all Microsoft email services so that your customers get proper notification that their messages cannot be responded to. Can you think of a better solution?
Leading to this unhelpful reply:
As previously stated, your IP(s) ... do not qualify for mitigation at this time. I do apologize, but I am unable to provide any details about this situation since we do not have the liberty to discuss the nature of the block.
Did you say Secret Blocks? Stay classy, Microsoft.

