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@angryox.com https://www.angryox.com/ ---------------------------------------------------------------------------

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@outages.org> On Behalf Of Peter Beckman via Outages Sent: Thursday, October 27, 2022 5:53 PM To: outages@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@angryox.com https://www.angryox.com/ --------------------------------------------------------------------------- _______________________________________________ Outages mailing list Outages@outages.org https://puck.nether.net/mailman/listinfo/outages

I hadn't found those, thank you Frank!! SERVICE SEEMS RECOVERED as of 8:09pm EDT Oct 27, 2022 It looks like lots of complaining finally got a change made -- the hotmail MX records have removed IPv6 AAAA records from DNS, and now all of our 945 delayed emails are delivered. The AAAA records were removed sometime between 6:49:28pm EDT and 8:13:52pm EDT. Logs show that sendmail stopped trying IPv6 at 8:09:11pm EDT and went back to IPv4, and then all emails were accepted finally. Thanks to whomever finally took action to resolve it! And please update all of your Email Service Provider functionality to support IPv6 BEFORE enabling it again please! Beckman On Thu, 27 Oct 2022, Frank Bulk via Outages wrote:
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@outages.org> On Behalf Of Peter Beckman via Outages Sent: Thursday, October 27, 2022 5:53 PM To: outages@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@angryox.com https://www.angryox.com/ --------------------------------------------------------------------------- _______________________________________________ Outages mailing list Outages@outages.org https://puck.nether.net/mailman/listinfo/outages
_______________________________________________ Outages mailing list Outages@outages.org https://puck.nether.net/mailman/listinfo/outages
--------------------------------------------------------------------------- Peter Beckman Internet Guy beckman@angryox.com https://www.angryox.com/ ---------------------------------------------------------------------------
participants (2)
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Frank Bulk
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Peter Beckman