Hi Laura (and all),

You are absolutely right. The trick is to set the SPF not for the domain but for the full EHLO string. Following the redacted information, I had the SPF for "maildomain.net", but not for "mailhost.maildomain.net". Emails coming from "dumbu...@maildomain.net" worked, but the notifications (with null sender) not.

I've created specific SPF entries for each of the outgoing EHLO string used (we have several outgoing hosts) and the vacation messages are going through.

Thanks a lot for your help.

Best regards.

El 27/8/24 a las 14:13, Laura Atkins via mailop escribió:
I trust Google to check SPF correctly, and can’t confirm that your system is correct because you’ve redacted any useful information. You’ve been told what to do (publish SPF for the domain in the EHLO value) and you’ve even been given the SPF string that will do it.

If you want assistance, don’t hide everything that will make it possible to give you that assistance.

laura



On 27 Aug 2024, at 13:09, Eduardo Diaz Comellas <ed...@ultreia.es> wrote:

Hi Laura,

Thanks for your help.  I've captured one of the SMTP transactions:


SMTP<< 220 mx.google.com ESMTP ffacd0b85a97d-37308269cdfsi4917634f8f.703 - gsmtp
 SMTP>> EHLO mailhost.maildomain.net
 SMTP<< 250-mx.google.com at your service, [555.555.555.555]
        250-SIZE 157286400
        250-8BITMIME
        250-STARTTLS
        250-ENHANCEDSTATUSCODES
        250-PIPELINING
        250-CHUNKING
        250 SMTPUTF8
 SMTP>> STARTTLS
 SMTP<< 220 2.0.0 Ready to start TLS
 SMTP>> EHLO mailhost.maildomain.net
 SMTP<< 250-mx.google.com at your service, [555.555.555.555]
        250-SIZE 157286400
        250-8BITMIME
        250-ENHANCEDSTATUSCODES
        250-PIPELINING
        250-CHUNKING
        250 SMTPUTF8
 SMTP>> MAIL FROM:<> SIZE=1862
 SMTP>> RCPT TO:<gmailu...@gmail.com>
        will write message using CHUNKING
 SMTP>> BDAT 646 LAST
 SMTP<< 250 2.1.0 OK ffacd0b85a97d-37308269cdfsi4917634f8f.703 - gsmtp
 SMTP<< 250 2.1.5 OK ffacd0b85a97d-37308269cdfsi4917634f8f.703 - gsmtp
 SMTP<< 550-5.7.26 Your email has been blocked because the sender is unauthenticated.         550-5.7.26 Gmail requires all senders to authenticate with either SPF or DKIM.
        550-5.7.26
        550-5.7.26  Authentication results:
        550-5.7.26  DKIM = did not pass
        550-5.7.26  SPF [] with ip: [555.555.555.555] = did not pass
        550-5.7.26
        550-5.7.26  For instructions on setting up authentication, go to
        550 5.7.26 https://support.google.com/mail/answer/81126#authentication ffacd0b85a97d-37308269cdfsi4917634f8f.703 - gsmtp
 SMTP>> QUIT
 SMTP(close)>>


I''ve double checked that the EHLO works with the SPF (in the redacted log, IP 555.555.555.555 matches maildomain.net's SPF):

<81XFvZGqU4hDuONl.png>

That is why I find this so weird.   I know DKIM is not setup there, but the SPF is and it is being ignored or not checked properly.

Best regards



On 27/8/24 13:28, Laura Atkins wrote:
You need to authenticate with either SPF or DKIM. As you’re using a null sender, you can set up SPF on the EHLO value. Or you can sign outgoing mail with DKIM, dealer’s choice.

laura

On 27 Aug 2024, at 11:56, Eduardo Diaz Comellas via mailop <mailop@mailop.org> wrote:

Hi all,

I've got a couple of complains from customers saying that the vacation message is not being received by Gmail users. Our email service is quite standard, with dovecot+sieve processing the email storage and autoresponders.

I've confirmed that the problem is true:

2024-08-27 11:08:09 1sisBN-002eWx-KM <= <> H=(mydovecot.host) [172.30.6.182] P=esmtp K S=1087 id=dovecot-sieve-1724749689-16845...@mydovecot.host 2024-08-27 11:08:10 1sisBN-002eWx-KM ** randomgmailu...@gmail.com R=hubbed_hosts T=remote_smtp H=gmail-smtp-in.l.google.com [173.194.76.27] X=TLS1.3:ECDHE_X25519__ECDSA_SECP256R1_SHA256__AES_256_GCM:256 CV=yes DN="CN=mx.google.com": SMTP error from remote mail server after pipelined end of data: 550-5.7.26 Your email has been blocked because the sender is unauthenticated.\n550-5.7.26 Gmail requires all senders to authenticate with either SPF or DKIM.\n550-5.7.26\n550-5.7.26  Authentication results:\n550-5.7.26  DKIM = did not pass\n550-5.7.26  SPF [] with ip: [555.555.555.555] = did not pass\n550-5.7.26\n550-5.7.26  For instructions on setting up authentication, go to\n550 5.7.26 https://support.google.com/mail/answer/81126#authentication ffacd0b8rr97d-373081420c7si4806836f8f.262 - gsmtp
2024-08-27 11:08:10 1sisBN-002eWx-KM Frozen (delivery error message)


I think that sending the vacation messages with null sender is an standard practise and the best way to avoid loops. I've found no problems with any other email providers: only gmail is blocking this messages.

Does anyone have this issue? How do you deal with it?

Best regards.

--
Eduardo Díaz Comellas
Ultreia Comunicaciones, S.L.

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--
The Delivery Expert

Laura Atkins
Word to the Wise
la...@wordtothewise.com

Delivery hints and commentary: http://wordtothewise.com/blog






--
Eduardo Díaz Comellas
Ultreia Comunicaciones, S.L.

--
The Delivery Expert

Laura Atkins
Word to the Wise
la...@wordtothewise.com

Delivery hints and commentary: http://wordtothewise.com/blog







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

--
Eduardo Díaz Comellas
Ultreia Comunicaciones, S.L.
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