Treat your sending MTA FQDNs as if they were separate customer domains, and 
configure SPF, DKIM and DMARC records for them.  You'll have no problems then.

Regards, 
Mark 

-- 
_________________________________________________________________ 
L. Mark Stone, Founder 
North America's Leading Zimbra VAR/BSP/Training Partner 
For Companies With Mission-Critical Email Needs

----- Original Message -----
| From: "Eduardo Diaz Comellas via mailop" <mailop@mailop.org>
| To: "mailop" <mailop@mailop.org>
| Sent: Tuesday, August 27, 2024 6:56:18 AM
| Subject: [mailop] Gmail not accepting bounces coming from vacation messages 
because of null sender and SPF/DKIM

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