Hi,

Wouldn't DKIM signing the OOF messages help? That way the authentication at 
gmail's side would not fail.

Regards
Norbert

-----Ursprüngliche Nachricht-----
Von: mailop <mailop-boun...@mailop.org> Im Auftrag von Marco Moock via mailop
Gesendet: Donnerstag, 15. August 2024 14:51
An: mailop@mailop.org
Cc: Kurt Jaeger <mai...@opsec.eu>
Betreff: Re: [mailop] gmail SPF check fail ?

Am 15.08.2024 um 14:35:35 Uhr schrieb Kurt Jaeger via mailop:

> Is it possible that gmail finds the <> envelope-from cheesy and
> choose to reject ?

No. If you use MAIL FROM: <>, the SPF doesn't work for MAIL FROM.

It will use the SPF (TXT) record for the domain name of the sending
SMTP server.
If that mail gets out by mail.example.org, mail.example.org will be
used for SPF, so TXT record for mail.example.org will be checked. Make
sure all outgoing SMTP servers have SPF TXT records for their domains.

-- 
Gruß
Marco

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