Out of office replies orginating from own Exchange to external, using DKIM, get blocked by destination

Jun 20, 2024
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Hello,


Also referring to this post, which seems to concern the same problem: https://forum.proxmox.com/threads/m...ffice-notification-from-exchange-2013.145482/

When Exchange (on-premise) sends an out of office (OOF) reply the envelope from (or return path) header is empty, which is correct by definition. Even when DKIM signing has been enabled in the Proxmox PMG these OOF e-mails do not get signed, I assume that this is because the envelope from header is empty and the DKIM-implementation does not revert to using the From:-header.

Example of an SMTP response we get from Gmail (grep from /var/log/mail.log):

2024-06-20T12:47:55.753705+02:00 VM-NL-SPAMFW-071 pmg-smtp-filter[2375663]: 601E4F667408DB9F0DC: accept mail to <xx@gmail.com> (AB98C601E69) (rule: default-accept)

2024-06-20T12:47:55.758887+02:00 VM-NL-SPAMFW-071 postfix/lmtp[2376271]: 8FCE9601D8E: to=<xx@gmail.com>, relay=127.0.0.1[127.0.0.1]:10023, delay=0.17, delays=0.02/0/0.05/0.11, dsn=2.5.0, status=sent (250 2.5.0 OK (601E4F667408DB9F0DC))

2024-06-20T12:47:56.075864+02:00 VM-NL-SPAMFW-071 postfix/smtp[2376332]: AB98C601E69: to=<xx@gmail.com>, relay=gmail-smtp-in.l.google.com[173.194.76.26]:25, delay=0.36, delays=0.05/0/0.08/0.23, dsn=5.7.26, status=bounced (host gmail-smtp-in.l.google.com[173.194.76.26] said: 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: [31.134.201.198] = 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-364b364c6absi724948f8f.819 - gsmtp (in reply to end of DATA command))


Can you help us out?


Kind regards,

Tijl Schoonenberg
 

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