My nifty plan of a sleep-in Sunday morning was destroyed by the puppy, unfortunately, leading me to traipse around the neighborhood with bedhead, Birkenstocks, and a bathrobe at 7am. So much for that.
Once I had corralled the dog, I came back in to grab a cup of coffee, and check my email. I found a love note from Microsoft Live/Hotmail, informing me that they had rejected a legitimate email from me to a Hotmail recipient for policy reasons. I suppose this is a better reaction than simply eating the email and not telling anyone, but barely. Their SMTP 5.1.1 error contained a link to contact them, so I did. That link (http://postmaster.live.com/) contains some interesting wording and interesting links, including this statement:
Q. Does Windows Live Hotmail operate an “allow list” that I can get on?
A. No. An allow list is essentially a “free pass” that allows e-mails from certain senders to bypass junk e-mail filters and other precautions. Windows Live Hotmail evaluates all inbound e-mail for malicious content. You can find out more about our filtering processes here.
There are a bevy of oddly-constructed pages that detail the myriad steps to be taken to actually send email to a Hotmail account. Then, there's the feedback form, where you can detail why you should be allowed to send email to Hotmail and Microsoft Live accounts. This feedback form assumes that you're running a mailing list (I'm not) and that you have a valid MX/DNS reverse record for the sending server.... except that this isn't possible when dealing with virtual domains on a single server, or multiple domains hosted behind a single egress IP. You can see the form right here.
Now, recall that I've already had to write custom destination rules for my mailserver to ship all Hotmail/Microsoft Live mail through my provider's SMTP gateway so that they wouldn't simply delete it. Now, they're rejecting even that email. How can you possibly justify this? Why bother providing the service at all if you're going to regularly change the rules and continue to delete legitimate inbound email?
For the record, the servers I run are not, and have never been involved in a bulk email/spam operation. Ever. Not once. They're not in any DNSBLs, or any other unsavory place. They are connected to the Internet via a business circuit, not a residential DSL or cable connection. The volume of mail from these servers to Hotmail/Microsoft Live is probably 0.25 messages per day.
Yet they can't send to Hotmail, even through a large volume, legitimate relay.
To further the absurdity, after filling out the Microsoft Junk Mail Reporting form I mentioned above, you get a page containing a ticket number, and this text:
"To make sure that you can receive a reply from Microsoft, add the "microsoft.com" domain to your e-mail "safe list". If you do not receive a response in your "inbox" within 24 hours, check your "bulk mail" or "junk mail" folders."
Oh, I see. Microsoft won't run an allow list, but I have to put them on mine to make sure that their response actually gets to me? It's a good thing that I didn't enter my Live.com or Hotmail.com address in the form -- we've already determined that receiving mail sent to those accounts is at best hit-or-miss. Again, it's painfully clear that Microsoft Live/Hotmail is simply not worth the time. Get Gmail, and get thee behind me, Hotmail.