[outages] Microsoft Hotmail Email Delivery Failures via IPv6

[Peter Beckman]

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