==== REQUIRED BASIC INFO OF YOUR IREDMAIL SERVER ====
- iRedMail version (check /etc/iredmail-release): 1.7.3
- Deployed with iRedMail Easy or the downloadable installer? iRedMail Enterprise
- Linux/BSD distribution name and version: Ubuntu 24.04
- Store mail accounts in which backend (LDAP/MySQL/PGSQL): LDAP
- Web server (Apache or Nginx): Nginx
- Manage mail accounts with iRedAdmin-Pro? iRedMail Enterprise
- [IMPORTANT] Related original log or error message is required if you're experiencing an issue.
====

An authenticated user on a whitelisted /24 tried to send myself and two other users an email. We are all on the same domain, served by this server. His MUA is configured to log in to send. I have the internal network we are both connected to on the system-wide whitelist, and on the Trusted Clients list.

The email he sent keeps getting marked as spam and discarded. I have spam quarantining turned on, but still, they are being discarded.

What can I do to turn off spam scanning on the sending side? And also, why is spam quarantining not working?

Here is a sanitized snippet of the mail log where his email is getting discarded (he is listed as sending.user@mydomain.com, and the three recipients are listed as receiving.user[1-3]@mydomain.com)

2025-06-25T12:06:31.072923+00:00 mail postfix/submission/smtpd[527454]: connect from unknown[192.168.11.133]
2025-06-25T12:06:31.075685+00:00 mail postfix/submission/smtpd[527454]: discarding EHLO keywords: CHUNKING
2025-06-25T12:06:31.135611+00:00 mail postfix/submission/smtpd[527454]: Anonymous TLS connection established from unknown[192.168.11.133]: TLSv1.2 with cipher ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
2025-06-25T12:06:31.137099+00:00 mail postfix/submission/smtpd[527454]: discarding EHLO keywords: CHUNKING
2025-06-25T12:06:31.211026+00:00 mail postfix/submission/smtpd[527454]: 4bS0sg1Tr1z7y5F4: client=unknown[192.168.11.133], sasl_method=PLAIN, sasl_username=sending.user@mydomain.com
2025-06-25T12:06:31.299819+00:00 mail postfix/cleanup[527456]: 4bS0sg1Tr1z7y5F4: message-id=<5FDA5420-5C64-44B5-A858-D99416894245@mydomain.com>
2025-06-25T12:06:31.320288+00:00 mail postfix/qmgr[1116177]: 4bS0sg1Tr1z7y5F4: from=<sending.user@mydomain.com>, size=561351, nrcpt=3 (queue active)
2025-06-25T12:06:38.054522+00:00 mail postfix/10025/smtpd[527479]: connect from mail.mydomain.com[127.0.0.1]
2025-06-25T12:06:38.054930+00:00 mail postfix/10025/smtpd[527479]: discarding EHLO keywords: CHUNKING
2025-06-25T12:06:38.063465+00:00 mail postfix/10025/smtpd[527479]: 4bS0sp0RNFz7y5FQ: client=mail.mydomain.com[127.0.0.1]
2025-06-25T12:06:38.067727+00:00 mail postfix/cleanup[527456]: 4bS0sp0RNFz7y5FQ: message-id=<SAIWgukn3tf2lw@mail.mydomain.com>
2025-06-25T12:06:38.068401+00:00 mail postfix/10025/smtpd[527480]: connect from mail.mydomain.com[127.0.0.1]
2025-06-25T12:06:38.068890+00:00 mail postfix/10025/smtpd[527480]: discarding EHLO keywords: CHUNKING
2025-06-25T12:06:38.069513+00:00 mail postfix/10025/smtpd[527479]: disconnect from mail.mydomain.com[127.0.0.1] ehlo=1 mail=1 rcpt=1 data=1 quit=1 commands=5
2025-06-25T12:06:38.070068+00:00 mail postfix/qmgr[1116177]: 4bS0sp0RNFz7y5FQ: from=<postmaster@mail.mydomain.com>, size=4836, nrcpt=1 (queue active)
2025-06-25T12:06:38.083172+00:00 mail amavis[330920]: (330920-14) Blocked SPAM {DiscardedInternal}, ORIGINATING LOCAL [192.168.11.133]:54693 ESMTP/ESMTP <sending.user@mydomain.com> -> <receiving.user2@mydomain.com>, (), Queue-ID: 4bS0sg1Tr1z7y5F4, Message-ID: <5FDA5420-5C64-44B5-A858-D99416894245@mydomain.com>, mail_id: IWgukn3tf2lw, b: 55v8LauJX, Hits: 6.964, size: 561350, Subject: "Fwd: Event in Paris May 31 to June 3", From: <sending.user@mydomain.com>, X-Mailer: Apple_Mail_(2.3826.600.51.1.1), helo=smtpclient.apple, Tests: [AC_DIV_BONANZA=0.001,ALL_TRUSTED=0.1,BAYES_50=0.8,HTML_FONT_LOW_CONTRAST=0.001,HTML_MESSAGE=0.3,KAM_DMARC_STATUS=0.01,KAM_INFOUSMEBIZ=0.75,KAM_NUMSUBJECT=0.5,KAM_SHORT=0.001,LOTS_OF_MONEY=4.5,XFER_LOTSA_MONEY=0.001], autolearn=no autolearn_force=no, autolearnscore=6.064, 6646 ms
2025-06-25T12:06:38.087289+00:00 mail postfix/amavis/smtp[527457]: 4bS0sg1Tr1z7y5F4: to=<receiving.user2@mydomain.com>, relay=127.0.0.1[127.0.0.1]:10026, delay=6.9, delays=0.17/0.12/0.01/6.6, dsn=2.7.0, status=sent (250 2.7.0 Ok, discarded, id=330920-14 - spam)
2025-06-25T12:06:38.093555+00:00 mail postfix/10025/smtpd[527480]: 4bS0sp0fSCz7y5FV: client=mail.mydomain.com[127.0.0.1]
2025-06-25T12:06:38.097706+00:00 mail postfix/cleanup[527456]: 4bS0sp0fSCz7y5FV: message-id=<SAFKhnN0s42jLn@mail.mydomain.com>
2025-06-25T12:06:38.099615+00:00 mail postfix/qmgr[1116177]: 4bS0sp0fSCz7y5FV: from=<postmaster@mail.mydomain.com>, size=4830, nrcpt=1 (queue active)
2025-06-25T12:06:38.100534+00:00 mail postfix/10025/smtpd[527480]: disconnect from mail.mydomain.com[127.0.0.1] ehlo=1 mail=1 rcpt=1 data=1 quit=1 commands=5
2025-06-25T12:06:38.103263+00:00 mail postfix/cleanup[527456]: 4bS0sp0hjbz7y5Fj: message-id=<SAIWgukn3tf2lw@mail.mydomain.com>
2025-06-25T12:06:38.104743+00:00 mail postfix/local[527482]: 4bS0sp0RNFz7y5FQ: to=<root@mail.mydomain.com>, relay=local, delay=0.04, delays=0.01/0.02/0/0.01, dsn=2.0.0, status=sent (forwarded as 4bS0sp0hjbz7y5Fj)
2025-06-25T12:06:38.104900+00:00 mail postfix/qmgr[1116177]: 4bS0sp0hjbz7y5Fj: from=<postmaster@mail.mydomain.com>, size=4989, nrcpt=1 (queue active)
2025-06-25T12:06:38.110388+00:00 mail postfix/qmgr[1116177]: 4bS0sp0RNFz7y5FQ: removed
2025-06-25T12:06:38.111173+00:00 mail amavis[339812]: (339812-12) Blocked SPAM {DiscardedInternal}, ORIGINATING LOCAL [192.168.11.133]:54693 ESMTP/ESMTP <sending.user@mydomain.com> -> <receiving.user3@mydomain.com>, (), Queue-ID: 4bS0sg1Tr1z7y5F4, Message-ID: <5FDA5420-5C64-44B5-A858-D99416894245@mydomain.com>, mail_id: FKhnN0s42jLn, b: 55v8LauJX, Hits: 6.964, size: 561350, Subject: "Fwd: Event in Paris May 31 to June 3", From: <sending.user@mydomain.com>, X-Mailer: Apple_Mail_(2.3826.600.51.1.1), helo=smtpclient.apple, Tests: [AC_DIV_BONANZA=0.001,ALL_TRUSTED=0.1,BAYES_50=0.8,HTML_FONT_LOW_CONTRAST=0.001,HTML_MESSAGE=0.3,KAM_DMARC_STATUS=0.01,KAM_INFOUSMEBIZ=0.75,KAM_NUMSUBJECT=0.5,KAM_SHORT=0.001,LOTS_OF_MONEY=4.5,XFER_LOTSA_MONEY=0.001], autolearn=no autolearn_force=no, autolearnscore=6.064, 6563 ms
2025-06-25T12:06:38.114246+00:00 mail postfix/amavis/smtp[527458]: 4bS0sg1Tr1z7y5F4: to=<receiving.user3@mydomain.com>, relay=127.0.0.1[127.0.0.1]:10026, delay=7, delays=0.17/0.23/0/6.6, dsn=2.7.0, status=sent (250 2.7.0 Ok, discarded, id=339812-12 - spam)
2025-06-25T12:06:38.116619+00:00 mail postfix/cleanup[527456]: 4bS0sp0mk6z7y5FQ: message-id=<SAFKhnN0s42jLn@mail.mydomain.com>
2025-06-25T12:06:38.118770+00:00 mail postfix/local[527482]: 4bS0sp0fSCz7y5FV: to=<root@mail.mydomain.com>, relay=local, delay=0.03, delays=0.01/0.01/0/0.01, dsn=2.0.0, status=sent (forwarded as 4bS0sp0mk6z7y5FQ)
2025-06-25T12:06:38.119008+00:00 mail postfix/qmgr[1116177]: 4bS0sp0mk6z7y5FQ: from=<postmaster@mail.mydomain.com>, size=4983, nrcpt=1 (queue active)
2025-06-25T12:06:38.119641+00:00 mail postfix/qmgr[1116177]: 4bS0sp0fSCz7y5FV: removed
2025-06-25T12:06:38.154083+00:00 mail postfix/10025/smtpd[527479]: connect from mail.mydomain.com[127.0.0.1]
2025-06-25T12:06:38.157494+00:00 mail postfix/10025/smtpd[527479]: discarding EHLO keywords: CHUNKING
2025-06-25T12:06:38.158783+00:00 mail postfix/10025/smtpd[527479]: 4bS0sp16Zxz7y5FV: client=mail.mydomain.com[127.0.0.1]
2025-06-25T12:06:38.163019+00:00 mail postfix/cleanup[527483]: 4bS0sp16Zxz7y5FV: message-id=<SAaZhJcNe2ljod@mail.mydomain.com>
2025-06-25T12:06:38.167789+00:00 mail postfix/10025/smtpd[527479]: disconnect from mail.mydomain.com[127.0.0.1] ehlo=1 mail=1 rcpt=1 data=1 quit=1 commands=5
2025-06-25T12:06:38.167933+00:00 mail postfix/qmgr[1116177]: 4bS0sp16Zxz7y5FV: from=<postmaster@mail.mydomain.com>, size=4831, nrcpt=1 (queue active)
2025-06-25T12:06:38.179146+00:00 mail amavis[339924]: (339924-12) Blocked SPAM {DiscardedInternal}, ORIGINATING LOCAL [192.168.11.133]:54693 ESMTP/ESMTP <sending.user@mydomain.com> -> <receiving.user1@mydomain.com>, (), Queue-ID: 4bS0sg1Tr1z7y5F4, Message-ID: <5FDA5420-5C64-44B5-A858-D99416894245@mydomain.com>, mail_id: aZhJcNe2ljod, b: 55v8LauJX, Hits: 6.964, size: 561350, Subject: "Fwd: Event in Paris May 31 to June 3", From: <sending.user@mydomain.com>, X-Mailer: Apple_Mail_(2.3826.600.51.1.1), helo=smtpclient.apple, Tests: [AC_DIV_BONANZA=0.001,ALL_TRUSTED=0.1,BAYES_50=0.8,HTML_FONT_LOW_CONTRAST=0.001,HTML_MESSAGE=0.3,KAM_DMARC_STATUS=0.01,KAM_INFOUSMEBIZ=0.75,KAM_NUMSUBJECT=0.5,KAM_SHORT=0.001,LOTS_OF_MONEY=4.5,XFER_LOTSA_MONEY=0.001], autolearn=no autolearn_force=no, autolearnscore=6.064, 6515 ms
2025-06-25T12:06:38.181707+00:00 mail postfix/cleanup[527456]: 4bS0sp1FsMz7y5Fv: message-id=<SAaZhJcNe2ljod@mail.mydomain.com>
2025-06-25T12:06:38.182883+00:00 mail postfix/amavis/smtp[527459]: 4bS0sg1Tr1z7y5F4: to=<receiving.user1@mydomain.com>, relay=127.0.0.1[127.0.0.1]:10026, delay=7, delays=0.17/0.34/0/6.5, dsn=2.7.0, status=sent (250 2.7.0 Ok, discarded, id=339924-12 - spam)