Hi Ralf,

We had the same problem few months back and i remember that was the action we took to mitigate the issue. I will state our dovecot `s submission proxy relevant config and hope that it will help.

```

auth_mechanisms = plain login

submission_max_mail_size = 30720000

submission_relay_host = smtp_ip

submission_relay_port = 587

submission_relay_trusted = yes

submission_relay_ssl = starttls

submission_relay_ssl_verify = no

submission_client_workarounds = whitespace-before-path

```

Our smtp server is running postfix. We use the following configuration for postfix`s master.cnf submission(port 587)

```

submission inet n       -       y       -       -       smtpd
  -o syslog_name=postfix/submission
  -o smtpd_tls_security_level=encrypt
  -o smtpd_sasl_auth_enable=yes
  -o smtpd_tls_auth_only=yes
  -o smtpd_reject_unlisted_recipient=no
#  -o smtpd_client_restrictions=$mua_client_restrictions
#  -o smtpd_helo_restrictions=$mua_helo_restrictions
  -o smtpd_sender_restrictions=$mua_sender_restrictions
  -o smtpd_recipient_restrictions=$mua_recipient_restrictions
  -o smtpd_relay_restrictions=$mua_relay_restrictions
  -o milter_macro_daemon_name=ORIGINATING
  -o smtpd_authorized_xclient_hosts=dovecot_host1_ip,dovecot_host2_ip
  -o smtpd_sasl_authenticated_header=no
  -o smtpd_sasl_path=smtpd
  -o smtpd_sasl_security_options=noanonymous
  -o smtpd_sasl_type=cyrus
  -o smtpd_sender_login_maps=$mua_sender_login_maps
  -o smtpd_tls_ciphers=high
  -o smtpd_tls_exclude_ciphers=$mua_exclude_ciphers
  -o smtpd_tls_mandatory_ciphers=high
  -o smtpd_tls_mandatory_exclude_ciphers=$mua_exclude_ciphers
  -o smtpd_tls_mandatory_protocols=$mua_tls_protocols
  -o smtpd_tls_protocols=$mua_tls_protocols
  -o smtpd_tls_received_header=yes
  -o tls_preempt_cipherlist=yes

```


On 22/5/23 16:25, Nikolaos Pyrgiotis wrote:

Have you tried adding the line below to your submision config?

submission_client_workarounds = whitespace-before-path
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