Not sure if this helps, but Gmail requires forward and reverse DNS for IPv6 to match.

Like this (example is from our own setup):

;; ANSWER SECTION:
e.1.7.0.0.0.0.0.0.0.0.0.0.0.0.0.a.1.e.7.0.0.4.f.1.1.1.0.1.0.a.2.ip6.arpa. 3379 IN PTR mail-db8eur05on2071e.outbound.protection.outlook.com.

;; ANSWER SECTION:
mail-db8eur05on2071e.outbound.protection.outlook.com. 76 IN AAAA 2a01:111:f400:7e1a::71e

However, the IPv6-address in the error below resolves to two names:

;; ANSWER SECTION:
0.0.7.0.0.0.0.0.0.0.0.0.0.0.0.0.b.1.6.2.3.0.4.f.1.1.1.0.1.0.a.2.ip6.arpa. 3165 IN PTR mail-cwxgbr01on20700.outbound.protection.outlook.com.

;; ANSWER SECTION:
mail-cwxgbr01on20700.outbound.protection.outlook.com. 24 IN AAAA 2a01:111:f403:707f::700 mail-cwxgbr01on20700.outbound.protection.outlook.com. 24 IN AAAA 2a01:111:f403:261b::700

If that is indeed an issue for Gmail, dan MS365 should perhaps fix this?

--
Marco


Op 24-04-2024 om 09:33 schreef Florian Effenberger via mailop:

Simon Branch via mailop wrote on 24.04.24 at 09:28:
/550 5.7.350 Remote server returned message detected as spam -> 550 5.7.1 [2a01:111:f403:261b::700 19] Gmail has detected that this message;is likely suspicious due to the very low reputation of the sending;domain. /

/To best protect our users from spam, the message has been;blocked. For more information, go to; https://support.google.com/mail/answer/188131 <https://support.google.com/mail/answer/188131> im8-20020a056214246800b00696b2e6b32asi14453219qvb.337 - gsmtp/

a friend of mine had a similar problem lately. DKIM, SPF, DMARC, PTR were all set up correctly, no blocklist entry.

He disabled IPv6 delivery to Google and could send his e-mails with IPv4, so "domain reputation" suggest something that might not be applicable, as the sending domain per se seemed fine.

I don't know how flexible you are in your configuration with MS365, but the error message suggests you connect to GMail via IPv6, so maybe the above helps.

Florian

Attachment: smime.p7s
Description: S/MIME-cryptografische ondertekening

_______________________________________________
mailop mailing list
mailop@mailop.org
https://list.mailop.org/listinfo/mailop

Reply via email to