[outages] Microsoft Hotmail Email Delivery Failures via IPv6

[Frank Bulk]

Yes, this has been discussed on mailops, twitter, and blogged about. =(
https://list.mailop.org/private/mailop/
https://twitter.com/dergrobi/status/1585008525167972352
https://www.spamresource.com/2022/10/problems-sending-to-microsoft-over-ipv6
.html
As far as I know, this is not fixed, yet?

Frank 

-----Original Message-----
From: Outages <outages-bounces at outages.org> On Behalf Of Peter Beckman via
Outages
Sent: Thursday, October 27, 2022 5:53 PM
To: outages at outages.org
Subject: [outages] Microsoft Hotmail Email Delivery Failures via IPv6

We have been using IPv6 for years, but hotmail has been IPv4.

Checking our email logs, we have been successfully delivering email via
IPv4 to Hotmail without issue since May 29, 2022 (as far back as our email
logs go at the moment).

At Oct 24 21:06:13 UTC, the MX record started returning IPv6 addresses:

 	hotmail.com.        3256    IN    MX    2
hotmail-com.olc.protection.outlook.com.

 	hotmail-com.olc.protection.outlook.com has address 104.47.1.33
 	hotmail-com.olc.protection.outlook.com has address 104.47.2.33
 	hotmail-com.olc.protection.outlook.com has IPv6 address
2a01:111:f400:7e8a::33
 	hotmail-com.olc.protection.outlook.com has IPv6 address
2a01:111:f400:7e89::33

So that's cool. Except that 54 minutes later, Hotmail blocked ALL of our
email
traffic.

     Deferred: 451 4.7.500 Server busy. Please try again later from
     [2a01:111:e400:7e0d::51]. (AS750)
     [HE1EUR04FT020.eop-eur04.prod.protection.outlook.com]

Pretty sure that the 9 (nine) emails we went via IPv6 at 5pm EDT did not
all get reported as SPAM.

To aggravate the situation further, Hotmail's Sender Tools are all still
IPv4-only. I cannot check or add or monitor an IPv6 address or range, and
their Support Tool also only allows IPv4 addresses.

I'm not an enterprise customer of Microsoft, but this is pretty crappy. I'm
now looking for ways to connect to Microsoft via IPv4 only while still
using IPv6 for other email systems.

Anyone else run into issues like this?

Beckman
---------------------------------------------------------------------------
Peter Beckman                                                  Internet Guy
beckman at angryox.com                                https://www.angryox.com/
---------------------------------------------------------------------------
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