1 (edited by szepczynski 2018-02-07 06:25:07)

Topic: Sender address rejected, please authenticate (in reply to RCPT TO com)

==== Required information ====
- iRedMail version (check /etc/iredmail-release): 
- Linux/BSD distribution name and version: 
- Store mail accounts in which backend (LDAP/MySQL/PGSQL): 
- Web server (Apache or Nginx):
- Manage mail accounts with iRedAdmin-Pro?
- [IMPORTANT] Related original log or error message is required if you're experiencing an issue.

I add second domain to my iredmail instance, configure DNS, check settings via mail-tester.com and I've got score close to 10/10.

For this issue let assume two domains:
domain1.com
domain2.com

When I send email from postmaster@domain1.com via gmail, the email is send correctly.
When I send email from some.account@domain2.com via gmail, the email is sent (and delivered), but I've got a reply from Mail Delivery System:

This is the mail system at host mail.mvpdoers.com.

I'm sorry to have to inform you that your message could not
be delivered to one or more recipients. It's attached below.

For further assistance, please send mail to postmaster.

If you do so, please include this problem report. You can
delete your own text from the attached returned message.

The mail system

<marcin@external-mail-server.com>: host external-mail-server.com[188.XX.XX.XX] said: 550
    5.1.8 Sender address rejected, please authenticate (in reply to RCPT TO
    command)

Logs Case 1 - mail delivered successful from postmaster@domain1.com

Log from /var/log/iredapd/iredapd.log

2018-02-06 22:59:44 DEBUG Connect from 127.0.0.1, port 52716.
2018-02-06 22:59:44 DEBUG smtp session: request=smtpd_access_policy
2018-02-06 22:59:44 DEBUG smtp session: protocol_state=RCPT
2018-02-06 22:59:44 DEBUG smtp session: protocol_name=ESMTP
2018-02-06 22:59:44 DEBUG smtp session: client_address=74.125.82.51
2018-02-06 22:59:44 DEBUG smtp session: client_name=mail-wm0-f51.google.com
2018-02-06 22:59:44 DEBUG smtp session: client_port=50350
2018-02-06 22:59:44 DEBUG smtp session: reverse_client_name=mail-wm0-f51.google.com
2018-02-06 22:59:44 DEBUG smtp session: helo_name=mail-wm0-f51.google.com
2018-02-06 22:59:44 DEBUG smtp session: sender=postmaster@domain1.com
2018-02-06 22:59:44 DEBUG smtp session: recipient=marcin@external-mail-server.com
2018-02-06 22:59:44 DEBUG smtp session: recipient_count=0
2018-02-06 22:59:44 DEBUG smtp session: queue_id=
2018-02-06 22:59:44 DEBUG smtp session: instance=2508.5a7a2550.94298.0
2018-02-06 22:59:44 DEBUG smtp session: size=1260
2018-02-06 22:59:44 DEBUG smtp session: etrn_domain=
2018-02-06 22:59:44 DEBUG smtp session: stress=
2018-02-06 22:59:44 DEBUG smtp session: sasl_method=PLAIN
2018-02-06 22:59:44 DEBUG smtp session: sasl_username=postmaster@domain1.com
2018-02-06 22:59:44 DEBUG smtp session: sasl_sender=
2018-02-06 22:59:44 DEBUG smtp session: ccert_subject=
2018-02-06 22:59:44 DEBUG smtp session: ccert_issuer=
2018-02-06 22:59:44 DEBUG smtp session: ccert_fingerprint=
2018-02-06 22:59:44 DEBUG smtp session: ccert_pubkey_fingerprint=
2018-02-06 22:59:44 DEBUG smtp session: encryption_protocol=TLSv1.2
2018-02-06 22:59:44 DEBUG smtp session: encryption_cipher=ECDHE-RSA-AES128-GCM-SHA256
2018-02-06 22:59:44 DEBUG smtp session: encryption_keysize=128
2018-02-06 22:59:44 DEBUG smtp session: policy_context=
2018-02-06 22:59:44 DEBUG --> Apply plugin: reject_null_sender
2018-02-06 22:59:44 DEBUG <-- Result: DUNNO
2018-02-06 22:59:44 DEBUG --> Apply plugin: wblist_rdns
2018-02-06 22:59:44 DEBUG Found SASL username, bypass rDNS check for outbound.
2018-02-06 22:59:44 DEBUG <-- Result: DUNNO
2018-02-06 22:59:44 DEBUG --> Apply plugin: reject_sender_login_mismatch
2018-02-06 22:59:44 DEBUG Sender: postmaster@domain1.com, SASL username: postmaster@domain1.com
2018-02-06 22:59:44 DEBUG SKIP: sender == sasl username.
2018-02-06 22:59:44 DEBUG <-- Result: DUNNO
2018-02-06 22:59:44 DEBUG --> Apply plugin: throttle
2018-02-06 22:59:44 DEBUG Check sender throttling.
2018-02-06 22:59:44 DEBUG [SQL] Query throttle setting:

        SELECT id, account, priority, period, max_msgs, max_quota, msg_size
          FROM throttle
         WHERE kind='outbound' AND account IN ('74.125.82.51', '@ip', 'postmaster@domain1.com', '@domain1.com', '@.', '@.domain1.com', '@.com', '74.125.82.*', '74.125.*.51')
         ORDER BY priority DESC

2018-02-06 22:59:44 DEBUG [SQL] Query result:
[]
2018-02-06 22:59:44 DEBUG No sender throttle setting.
2018-02-06 22:59:44 DEBUG Bypass recipient throttling (found sasl_username).
2018-02-06 22:59:44 DEBUG <-- Result: DUNNO
2018-02-06 22:59:44 DEBUG --> Apply plugin: sql_alias_access_policy
2018-02-06 22:59:44 DEBUG [SQL] query access policy:
SELECT accesspolicy
               FROM alias
              WHERE address='marcin@external-mail-server.com'
              LIMIT 1
2018-02-06 22:59:44 DEBUG SQL query result: None
2018-02-06 22:59:44 DEBUG [SQL] Check whether recipient domain is an alias domain:
SELECT target_domain
                   FROM alias_domain
                  WHERE alias_domain = 'external-mail-server.com'
                  LIMIT 1

2018-02-06 22:59:44 DEBUG [SQL] Query result: None
2018-02-06 22:59:44 DEBUG Recipient domain is not an alias domain.
2018-02-06 22:59:44 DEBUG <-- Result: DUNNO Recipient is not a mail alias account or no access policy
2018-02-06 22:59:44 DEBUG --> Apply plugin: amavisd_wblist
2018-02-06 22:59:44 DEBUG Possible policy senders: ['postmaster@domain1.com', '@domain1.com', '@.', '@.domain1.com', '@.com', '74.125.82.51', '74.125.82.*', '74.125.*.51']
2018-02-06 22:59:44 DEBUG Possible policy recipients: ['marcin@external-mail-server.com', '@external-mail-server.com', '@.', '@.external-mail-server.com', '@.pl']
2018-02-06 22:59:44 DEBUG Apply wblist for outbound message.
2018-02-06 22:59:44 DEBUG [SQL] Query local addresses:
SELECT id, email
               FROM users
              WHERE email IN ('postmaster@domain1.com', '@domain1.com', '@.', '@.domain1.com', '@.com', '74.125.82.51', '74.125.82.*', '74.125.*.51')
           ORDER BY priority DESC
2018-02-06 22:59:44 DEBUG Local addresses (in `users`): [(1, '@.')]
2018-02-06 22:59:44 DEBUG [SQL] Query external addresses:
SELECT id, email
               FROM mailaddr
              WHERE email IN ('marcin@external-mail-server.com', '@external-mail-server.com', '@.', '@.external-mail-server.com', '@.pl')
           ORDER BY priority DESC
2018-02-06 22:59:44 DEBUG No record found in SQL database.
2018-02-06 22:59:44 DEBUG [SQL] Query CIDR network:
SELECT id, email
               FROM mailaddr
              WHERE email LIKE '74.%%'
           ORDER BY priority DESC
2018-02-06 22:59:44 DEBUG No valid sender id or recipient id.
2018-02-06 22:59:44 DEBUG [SQL] query local domain (external-mail-server.com):
SELECT domain
                   FROM domain
                  WHERE domain='external-mail-server.com'
                  LIMIT 1
2018-02-06 22:59:44 DEBUG SQL query result: None
2018-02-06 22:59:44 DEBUG [SQL] query alias domains (external-mail-server.com):
SELECT alias_domain
                   FROM alias_domain
                  WHERE alias_domain='external-mail-server.com' OR target_domain='external-mail-server.com'
                  LIMIT 1
2018-02-06 22:59:44 DEBUG SQL query result: None
2018-02-06 22:59:44 DEBUG <-- Result: DUNNO
2018-02-06 22:59:44 DEBUG Session ended.
2018-02-06 22:59:44 INFO [74.125.82.51] RCPT, postmaster@domain1.com => marcin@external-mail-server.com, DUNNO [0.0072s]
2018-02-06 22:59:44 DEBUG smtp session: request=smtpd_access_policy
2018-02-06 22:59:44 DEBUG smtp session: protocol_state=END-OF-MESSAGE
2018-02-06 22:59:44 DEBUG smtp session: protocol_name=ESMTP
2018-02-06 22:59:44 DEBUG smtp session: client_address=74.125.82.51
2018-02-06 22:59:44 DEBUG smtp session: client_name=mail-wm0-f51.google.com
2018-02-06 22:59:44 DEBUG smtp session: client_port=50350
2018-02-06 22:59:44 DEBUG smtp session: reverse_client_name=mail-wm0-f51.google.com
2018-02-06 22:59:44 DEBUG smtp session: helo_name=mail-wm0-f51.google.com
2018-02-06 22:59:44 DEBUG smtp session: sender=postmaster@domain1.com
2018-02-06 22:59:44 DEBUG smtp session: recipient=marcin@external-mail-server.com
2018-02-06 22:59:44 DEBUG smtp session: recipient_count=1
2018-02-06 22:59:44 DEBUG smtp session: queue_id=9F2501C0B11
2018-02-06 22:59:44 DEBUG smtp session: instance=2508.5a7a2550.94298.0
2018-02-06 22:59:44 DEBUG smtp session: size=1260
2018-02-06 22:59:44 DEBUG smtp session: etrn_domain=
2018-02-06 22:59:44 DEBUG smtp session: stress=
2018-02-06 22:59:44 DEBUG smtp session: sasl_method=PLAIN
2018-02-06 22:59:44 DEBUG smtp session: sasl_username=postmaster@domain1.com
2018-02-06 22:59:44 DEBUG smtp session: sasl_sender=
2018-02-06 22:59:44 DEBUG smtp session: ccert_subject=
2018-02-06 22:59:44 DEBUG smtp session: ccert_issuer=
2018-02-06 22:59:44 DEBUG smtp session: ccert_fingerprint=
2018-02-06 22:59:44 DEBUG smtp session: ccert_pubkey_fingerprint=
2018-02-06 22:59:44 DEBUG smtp session: encryption_protocol=TLSv1.2
2018-02-06 22:59:44 DEBUG smtp session: encryption_cipher=ECDHE-RSA-AES128-GCM-SHA256
2018-02-06 22:59:44 DEBUG smtp session: encryption_keysize=128
2018-02-06 22:59:44 DEBUG smtp session: policy_context=
2018-02-06 22:59:44 DEBUG Skip plugin: reject_null_sender (protocol_state != END-OF-MESSAGE)
2018-02-06 22:59:44 DEBUG Skip plugin: wblist_rdns (protocol_state != END-OF-MESSAGE)
2018-02-06 22:59:44 DEBUG Skip plugin: reject_sender_login_mismatch (protocol_state != END-OF-MESSAGE)
2018-02-06 22:59:44 DEBUG --> Apply plugin: throttle
2018-02-06 22:59:44 DEBUG Check sender throttling.
2018-02-06 22:59:44 DEBUG [SQL] Query throttle setting:

        SELECT id, account, priority, period, max_msgs, max_quota, msg_size
          FROM throttle
         WHERE kind='outbound' AND account IN ('74.125.82.51', '@ip', 'postmaster@domain1.com', '@domain1.com', '@.', '@.domain1.com', '@.com', '74.125.82.*', '74.125.*.51')
         ORDER BY priority DESC

2018-02-06 22:59:44 DEBUG [SQL] Query result:
[]
2018-02-06 22:59:44 DEBUG No sender throttle setting.
2018-02-06 22:59:44 DEBUG Bypass recipient throttling (found sasl_username).
2018-02-06 22:59:44 DEBUG <-- Result: DUNNO
2018-02-06 22:59:44 DEBUG Skip plugin: sql_alias_access_policy (protocol_state != END-OF-MESSAGE)
2018-02-06 22:59:44 DEBUG Skip plugin: amavisd_wblist (protocol_state != END-OF-MESSAGE)
2018-02-06 22:59:44 DEBUG Session ended.
2018-02-06 22:59:44 INFO [74.125.82.51] END-OF-MESSAGE, postmaster@domain1.com => marcin@external-mail-server.com, DUNNO [0.0019s]

Log from /var/log/postfix

Feb  6 22:59:44 mail postfix/submission/smtpd[9480]: connect from mail-wm0-f51.google.com[74.125.82.51]
Feb  6 22:59:44 mail postfix/submission/smtpd[9480]: Anonymous TLS connection established from mail-wm0-f51.google.com[74.125.82.51]: TLSv1.2 with cipher ECDHE-RSA-AES128-GCM-SHA256 (128/128 bits)
Feb  6 22:59:44 mail postfix/submission/smtpd[9480]: 9F2501C0B11: client=mail-wm0-f51.google.com[74.125.82.51], sasl_method=PLAIN, sasl_username=postmaster@domain1.com
Feb  6 22:59:44 mail postfix/cleanup[9489]: 9F2501C0B11: message-id=<CAGbp93tM+uB=QknDwV=TR-_YL3LWj+qFnPOBz1ZnZsT2PXKhJg@mail.gmail.com>
Feb  6 22:59:44 mail postfix/qmgr[5093]: 9F2501C0B11: from=<postmaster@domain1.com>, size=1473, nrcpt=1 (queue active)
Feb  6 22:59:44 mail postfix/submission/smtpd[9480]: disconnect from mail-wm0-f51.google.com[74.125.82.51] ehlo=2 starttls=1 auth=1 mail=1 rcpt=1 data=1 quit=1 commands=8
Feb  6 22:59:45 mail postfix/10025/smtpd[9499]: connect from localhost[127.0.0.1]
Feb  6 22:59:45 mail postfix/10025/smtpd[9499]: A11241C0B1F: client=localhost[127.0.0.1]
Feb  6 22:59:45 mail postfix/cleanup[9489]: A11241C0B1F: message-id=<CAGbp93tM+uB=QknDwV=TR-_YL3LWj+qFnPOBz1ZnZsT2PXKhJg@mail.gmail.com>
Feb  6 22:59:45 mail postfix/qmgr[5093]: A11241C0B1F: from=<postmaster@domain1.com>, size=2535, nrcpt=1 (queue active)
Feb  6 22:59:45 mail amavis[2102]: (02102-04) Passed CLEAN {RelayedInternal}, ORIGINATING LOCAL [74.125.82.51]:50350 [74.125.82.51] <postmaster@domain1.com> -> <marcin@external-mail-server.com>, Queue-ID: 9F2501C0B11, Message-ID: <CAGbp93tM+uB=QknDwV=TR-_YL3LWj+qFnPOBz1ZnZsT2PXKhJg@mail.gmail.com>, mail_id: 73HOrY8VnkgU, Hits: -0.999, size: 1473, queued_as: A11241C0B1F, dkim_new=dkim:domain1.com, 1007 ms, Tests: [ALL_TRUSTED=-1,HTML_MESSAGE=0.001]
Feb  6 22:59:45 mail postfix/10025/smtpd[9499]: disconnect from localhost[127.0.0.1] ehlo=1 mail=1 rcpt=1 data=1 quit=1 commands=5
Feb  6 22:59:45 mail postfix/amavis/smtp[9494]: 9F2501C0B11: to=<marcin@external-mail-server.com>, relay=127.0.0.1[127.0.0.1]:10026, delay=1.1, delays=0.09/0.01/0/1, dsn=2.0.0, status=sent (250 2.0.0 from MTA(smtp:[127.0.0.1]:10025): 250 2.0.0 Ok: queued as A11241C0B1F)
Feb  6 22:59:45 mail postfix/qmgr[5093]: 9F2501C0B11: removed
Feb  6 22:59:46 mail postfix/smtp[9500]: Untrusted TLS connection established to external-mail-server.com[188.XX.XX.XX]:25: TLSv1.2 with cipher ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
Feb  6 22:59:46 mail postfix/smtp[9500]: A11241C0B1F: to=<marcin@external-mail-server.com>, relay=external-mail-server.com[188.XX.XX.XX]:25, delay=0.48, delays=0.05/0.01/0.32/0.1, dsn=2.0.0, status=sent (250 2.0.0 Message accepted.)
Feb  6 22:59:46 mail postfix/qmgr[5093]: A11241C0B1F: removed

Logs Case 2 - mail delivered, but notice from Mail Delivery System some.account@domain2.com

Log from /var/log/iredapd/iredapd.log

2018-02-06 23:13:48 DEBUG Connect from 127.0.0.1, port 54766.
2018-02-06 23:13:48 DEBUG smtp session: request=smtpd_access_policy
2018-02-06 23:13:48 DEBUG smtp session: protocol_state=RCPT
2018-02-06 23:13:48 DEBUG smtp session: protocol_name=ESMTP
2018-02-06 23:13:48 DEBUG smtp session: client_address=74.125.82.43
2018-02-06 23:13:48 DEBUG smtp session: client_name=mail-wm0-f43.google.com
2018-02-06 23:13:48 DEBUG smtp session: client_port=39026
2018-02-06 23:13:48 DEBUG smtp session: reverse_client_name=mail-wm0-f43.google.com
2018-02-06 23:13:48 DEBUG smtp session: helo_name=mail-wm0-f43.google.com
2018-02-06 23:13:48 DEBUG smtp session: sender=some.account@domain2.com
2018-02-06 23:13:48 DEBUG smtp session: recipient=marcin@external-mail-server.com
2018-02-06 23:13:48 DEBUG smtp session: recipient_count=0
2018-02-06 23:13:48 DEBUG smtp session: queue_id=
2018-02-06 23:13:48 DEBUG smtp session: instance=2e8c.5a7a289c.b16a3.0
2018-02-06 23:13:48 DEBUG smtp session: size=3057
2018-02-06 23:13:48 DEBUG smtp session: etrn_domain=
2018-02-06 23:13:48 DEBUG smtp session: stress=
2018-02-06 23:13:48 DEBUG smtp session: sasl_method=PLAIN
2018-02-06 23:13:48 DEBUG smtp session: sasl_username=some.account@domain2.com
2018-02-06 23:13:48 DEBUG smtp session: sasl_sender=
2018-02-06 23:13:48 DEBUG smtp session: ccert_subject=
2018-02-06 23:13:48 DEBUG smtp session: ccert_issuer=
2018-02-06 23:13:48 DEBUG smtp session: ccert_fingerprint=
2018-02-06 23:13:48 DEBUG smtp session: ccert_pubkey_fingerprint=
2018-02-06 23:13:48 DEBUG smtp session: encryption_protocol=TLSv1.2
2018-02-06 23:13:48 DEBUG smtp session: encryption_cipher=ECDHE-RSA-AES128-GCM-SHA256
2018-02-06 23:13:48 DEBUG smtp session: encryption_keysize=128
2018-02-06 23:13:48 DEBUG smtp session: policy_context=
2018-02-06 23:13:48 DEBUG --> Apply plugin: reject_null_sender
2018-02-06 23:13:48 DEBUG <-- Result: DUNNO
2018-02-06 23:13:48 DEBUG --> Apply plugin: wblist_rdns
2018-02-06 23:13:48 DEBUG Found SASL username, bypass rDNS check for outbound.
2018-02-06 23:13:48 DEBUG <-- Result: DUNNO
2018-02-06 23:13:48 DEBUG --> Apply plugin: reject_sender_login_mismatch
2018-02-06 23:13:48 DEBUG Sender: some.account@domain2.com, SASL username: some.account@domain2.com
2018-02-06 23:13:48 DEBUG SKIP: sender == sasl username.
2018-02-06 23:13:48 DEBUG <-- Result: DUNNO
2018-02-06 23:13:48 DEBUG --> Apply plugin: throttle
2018-02-06 23:13:48 DEBUG Check sender throttling.
2018-02-06 23:13:48 DEBUG [SQL] Query throttle setting:

        SELECT id, account, priority, period, max_msgs, max_quota, msg_size
          FROM throttle
         WHERE kind='outbound' AND account IN ('74.125.82.43', '@ip', 'some.account@domain2.com', '@domain2.com', '@.', '@.domain2.com', '@.com', '74.125.82.*', '74.125.*.43')
         ORDER BY priority DESC

2018-02-06 23:13:48 DEBUG [SQL] Query result:
[]
2018-02-06 23:13:48 DEBUG No sender throttle setting.
2018-02-06 23:13:48 DEBUG Bypass recipient throttling (found sasl_username).
2018-02-06 23:13:48 DEBUG <-- Result: DUNNO
2018-02-06 23:13:48 DEBUG --> Apply plugin: sql_alias_access_policy
2018-02-06 23:13:48 DEBUG [SQL] query access policy:
SELECT accesspolicy
               FROM alias
              WHERE address='marcin@external-mail-server.com'
              LIMIT 1
2018-02-06 23:13:48 DEBUG SQL query result: None
2018-02-06 23:13:48 DEBUG [SQL] Check whether recipient domain is an alias domain:
SELECT target_domain
                   FROM alias_domain
                  WHERE alias_domain = 'external-mail-server.com'
                  LIMIT 1

2018-02-06 23:13:48 DEBUG [SQL] Query result: None
2018-02-06 23:13:48 DEBUG Recipient domain is not an alias domain.
2018-02-06 23:13:48 DEBUG <-- Result: DUNNO Recipient is not a mail alias account or no access policy
2018-02-06 23:13:48 DEBUG --> Apply plugin: amavisd_wblist
2018-02-06 23:13:48 DEBUG Possible policy senders: ['some.account@domain2.com', '@domain2.com', '@.', '@.domain2.com', '@.com', '74.125.82.43', '74.125.82.*', '74.125.*.43']
2018-02-06 23:13:48 DEBUG Possible policy recipients: ['marcin@external-mail-server.com', '@external-mail-server.com', '@.', '@.external-mail-server.com', '@.pl']
2018-02-06 23:13:48 DEBUG Apply wblist for outbound message.
2018-02-06 23:13:48 DEBUG [SQL] Query local addresses:
SELECT id, email
               FROM users
              WHERE email IN ('some.account@domain2.com', '@domain2.com', '@.', '@.domain2.com', '@.com', '74.125.82.43', '74.125.82.*', '74.125.*.43')
           ORDER BY priority DESC
2018-02-06 23:13:48 DEBUG Local addresses (in `users`): [(1, '@.')]
2018-02-06 23:13:48 DEBUG [SQL] Query external addresses:
SELECT id, email
               FROM mailaddr
              WHERE email IN ('marcin@external-mail-server.com', '@external-mail-server.com', '@.', '@.external-mail-server.com', '@.pl')
           ORDER BY priority DESC
2018-02-06 23:13:48 DEBUG No record found in SQL database.
2018-02-06 23:13:48 DEBUG [SQL] Query CIDR network:
SELECT id, email
               FROM mailaddr
              WHERE email LIKE '74.%%'
           ORDER BY priority DESC
2018-02-06 23:13:48 DEBUG No valid sender id or recipient id.
2018-02-06 23:13:48 DEBUG [SQL] query local domain (external-mail-server.com):
SELECT domain
                   FROM domain
                  WHERE domain='external-mail-server.com'
                  LIMIT 1
2018-02-06 23:13:48 DEBUG SQL query result: None
2018-02-06 23:13:48 DEBUG [SQL] query alias domains (external-mail-server.com):
SELECT alias_domain
                   FROM alias_domain
                  WHERE alias_domain='external-mail-server.com' OR target_domain='external-mail-server.com'
                  LIMIT 1
2018-02-06 23:13:48 DEBUG SQL query result: None
2018-02-06 23:13:48 DEBUG <-- Result: DUNNO
2018-02-06 23:13:48 DEBUG Session ended.
2018-02-06 23:13:48 INFO [74.125.82.43] RCPT, some.account@domain2.com => marcin@external-mail-server.com, DUNNO [0.0093s]
2018-02-06 23:13:48 DEBUG smtp session: request=smtpd_access_policy
2018-02-06 23:13:48 DEBUG smtp session: protocol_state=END-OF-MESSAGE
2018-02-06 23:13:48 DEBUG smtp session: protocol_name=ESMTP
2018-02-06 23:13:48 DEBUG smtp session: client_address=74.125.82.43
2018-02-06 23:13:48 DEBUG smtp session: client_name=mail-wm0-f43.google.com
2018-02-06 23:13:48 DEBUG smtp session: client_port=39026
2018-02-06 23:13:48 DEBUG smtp session: reverse_client_name=mail-wm0-f43.google.com
2018-02-06 23:13:48 DEBUG smtp session: helo_name=mail-wm0-f43.google.com
2018-02-06 23:13:48 DEBUG smtp session: sender=some.account@domain2.com
2018-02-06 23:13:48 DEBUG smtp session: recipient=marcin@external-mail-server.com
2018-02-06 23:13:48 DEBUG smtp session: recipient_count=1
2018-02-06 23:13:48 DEBUG smtp session: queue_id=B5FDF1C0B1C
2018-02-06 23:13:48 DEBUG smtp session: instance=2e8c.5a7a289c.b16a3.0
2018-02-06 23:13:48 DEBUG smtp session: size=3057
2018-02-06 23:13:48 DEBUG smtp session: etrn_domain=
2018-02-06 23:13:48 DEBUG smtp session: stress=
2018-02-06 23:13:48 DEBUG smtp session: sasl_method=PLAIN
2018-02-06 23:13:48 DEBUG smtp session: sasl_username=some.account@domain2.com
2018-02-06 23:13:48 DEBUG smtp session: sasl_sender=
2018-02-06 23:13:48 DEBUG smtp session: ccert_subject=
2018-02-06 23:13:48 DEBUG smtp session: ccert_issuer=
2018-02-06 23:13:48 DEBUG smtp session: ccert_fingerprint=
2018-02-06 23:13:48 DEBUG smtp session: ccert_pubkey_fingerprint=
2018-02-06 23:13:48 DEBUG smtp session: encryption_protocol=TLSv1.2
2018-02-06 23:13:48 DEBUG smtp session: encryption_cipher=ECDHE-RSA-AES128-GCM-SHA256
2018-02-06 23:13:48 DEBUG smtp session: encryption_keysize=128
2018-02-06 23:13:48 DEBUG smtp session: policy_context=
2018-02-06 23:13:48 DEBUG Skip plugin: reject_null_sender (protocol_state != END-OF-MESSAGE)
2018-02-06 23:13:48 DEBUG Skip plugin: wblist_rdns (protocol_state != END-OF-MESSAGE)
2018-02-06 23:13:48 DEBUG Skip plugin: reject_sender_login_mismatch (protocol_state != END-OF-MESSAGE)
2018-02-06 23:13:48 DEBUG --> Apply plugin: throttle
2018-02-06 23:13:48 DEBUG Check sender throttling.
2018-02-06 23:13:48 DEBUG [SQL] Query throttle setting:

        SELECT id, account, priority, period, max_msgs, max_quota, msg_size
          FROM throttle
         WHERE kind='outbound' AND account IN ('74.125.82.43', '@ip', 'some.account@domain2.com', '@domain2.com', '@.', '@.domain2.com', '@.com', '74.125.82.*', '74.125.*.43')
         ORDER BY priority DESC

2018-02-06 23:13:48 DEBUG [SQL] Query result:
[]
2018-02-06 23:13:48 DEBUG No sender throttle setting.
2018-02-06 23:13:48 DEBUG Bypass recipient throttling (found sasl_username).
2018-02-06 23:13:48 DEBUG <-- Result: DUNNO
2018-02-06 23:13:48 DEBUG Skip plugin: sql_alias_access_policy (protocol_state != END-OF-MESSAGE)
2018-02-06 23:13:48 DEBUG Skip plugin: amavisd_wblist (protocol_state != END-OF-MESSAGE)
2018-02-06 23:13:48 DEBUG Session ended.
2018-02-06 23:13:48 INFO [74.125.82.43] END-OF-MESSAGE, some.account@domain2.com => marcin@external-mail-server.com, DUNNO [0.0028s]

Log from /var/log/postfix

Feb  6 23:13:48 mail postfix/submission/smtpd[11916]: connect from mail-wm0-f43.google.com[74.125.82.43]
Feb  6 23:13:48 mail postfix/submission/smtpd[11916]: Anonymous TLS connection established from mail-wm0-f43.google.com[74.125.82.43]: TLSv1.2 with cipher ECDHE-RSA-AES128-GCM-SHA256 (128/128 bits)
Feb  6 23:13:48 mail postfix/submission/smtpd[11916]: B5FDF1C0B1C: client=mail-wm0-f43.google.com[74.125.82.43], sasl_method=PLAIN, sasl_username=some.account@domain2.com
Feb  6 23:13:48 mail postfix/cleanup[11924]: B5FDF1C0B1C: message-id=<CAGbp93uLfpBPCtNLGNKV4+BgfUyG2WHcrQo-wM6FvYpTN2pNYA@mail.gmail.com>
Feb  6 23:13:48 mail postfix/qmgr[5093]: B5FDF1C0B1C: from=<some.account@domain2.com>, size=3270, nrcpt=1 (queue active)
Feb  6 23:13:48 mail postfix/submission/smtpd[11916]: disconnect from mail-wm0-f43.google.com[74.125.82.43] ehlo=2 starttls=1 auth=1 mail=1 rcpt=1 data=1 quit=1 commands=8
Feb  6 23:13:49 mail postfix/10025/smtpd[11934]: connect from localhost[127.0.0.1]
Feb  6 23:13:49 mail postfix/10025/smtpd[11934]: 938071C0B1F: client=localhost[127.0.0.1]
Feb  6 23:13:49 mail postfix/cleanup[11924]: 938071C0B1F: message-id=<CAGbp93uLfpBPCtNLGNKV4+BgfUyG2WHcrQo-wM6FvYpTN2pNYA@mail.gmail.com>
Feb  6 23:13:49 mail postfix/qmgr[5093]: 938071C0B1F: from=<some.account@domain2.com>, size=4332, nrcpt=1 (queue active)
Feb  6 23:13:49 mail amavis[2098]: (02098-03) Passed CLEAN {RelayedInternal}, ORIGINATING LOCAL [74.125.82.43]:39026 [74.125.82.43] <some.account@domain2.com> -> <marcin@external-mail-server.com>, Queue-ID: B5FDF1C0B1C, Message-ID: <CAGbp93uLfpBPCtNLGNKV4+BgfUyG2WHcrQo-wM6FvYpTN2pNYA@mail.gmail.com>, mail_id: 54Gps_NM1BGs, Hits: 0.318, size: 3270, queued_as: 938071C0B1F, dkim_new=dkim:cutmypage.com, 828 ms, Tests: [ALL_TRUSTED=-1,HTML_IMAGE_ONLY_16=1.048,HTML_MESSAGE=0.001,HTML_SHORT_LINK_IMG_2=0.259,T_REMOTE_IMAGE=0.01]
Feb  6 23:13:49 mail postfix/10025/smtpd[11934]: disconnect from localhost[127.0.0.1] ehlo=1 mail=1 rcpt=1 data=1 quit=1 commands=5
Feb  6 23:13:49 mail postfix/amavis/smtp[11929]: B5FDF1C0B1C: to=<marcin@external-mail-server.com>, relay=127.0.0.1[127.0.0.1]:10026, delay=0.97, delays=0.09/0.01/0/0.87, dsn=2.0.0, status=sent (250 2.0.0 from MTA(smtp:[127.0.0.1]:10025): 250 2.0.0 Ok: queued as 938071C0B1F)
Feb  6 23:13:49 mail postfix/qmgr[5093]: B5FDF1C0B1C: removed
Feb  6 23:13:49 mail postfix/smtp[11935]: Untrusted TLS connection established to external-mail-server.com[188.XX.XX.XX]:25: TLSv1.2 with cipher ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
Feb  6 23:13:49 mail postfix/smtp[11935]: 938071C0B1F: to=<marcin@external-mail-server.com>, relay=external-mail-server.com[188.XX.XX.XX]:25, delay=0.33, delays=0.05/0.01/0.2/0.07, dsn=5.1.8, status=bounced (host external-mail-server.com[188.XX.XX.XX] said: 550 5.1.8 Sender address rejected, please authenticate (in reply to RCPT TO command))
Feb  6 23:13:49 mail postfix/cleanup[11924]: EAAF51C0B20: message-id=<20180206221349.EAAF51C0B20@mail.domain2.com>
Feb  6 23:13:50 mail postfix/qmgr[5093]: EAAF51C0B20: from=<>, size=6477, nrcpt=1 (queue active)
Feb  6 23:13:50 mail postfix/bounce[11936]: 938071C0B1F: sender non-delivery notification: EAAF51C0B20
Feb  6 23:13:50 mail postfix/qmgr[5093]: 938071C0B1F: removed
Feb  6 23:13:50 mail postfix/pickup[5092]: 0A63C1C0B1F: uid=2000 from=<MAILER-DAEMON>
Feb  6 23:13:50 mail postfix/cleanup[11924]: 0A63C1C0B1F: message-id=<20180206221349.EAAF51C0B20@mail.domain2.com>
Feb  6 23:13:50 mail postfix/pipe[11937]: EAAF51C0B20: to=<some.account@domain2.com>, relay=dovecot, delay=0.09, delays=0.04/0.01/0/0.04, dsn=2.0.0, status=sent (delivered via dovecot service)
Feb  6 23:13:50 mail postfix/qmgr[5093]: EAAF51C0B20: removed
Feb  6 23:13:50 mail postfix/qmgr[5093]: 0A63C1C0B1F: from=<>, size=6742, nrcpt=1 (queue active)
Feb  6 23:13:50 mail postfix/10025/smtpd[11934]: connect from localhost[127.0.0.1]
Feb  6 23:13:50 mail postfix/10025/smtpd[11934]: A7A291C0B1C: client=localhost[127.0.0.1]
Feb  6 23:13:50 mail postfix/cleanup[11924]: A7A291C0B1C: message-id=<20180206221349.EAAF51C0B20@mail.domain2.com>
Feb  6 23:13:50 mail postfix/qmgr[5093]: A7A291C0B1C: from=<>, size=7204, nrcpt=1 (queue active)
Feb  6 23:13:50 mail postfix/10025/smtpd[11934]: disconnect from localhost[127.0.0.1] ehlo=1 mail=1 rcpt=1 data=1 quit=1 commands=5
Feb  6 23:13:50 mail amavis[2100]: (02100-04) Passed CLEAN {RelayedInbound}, [127.0.0.1] <> -> <my-gmail-account@gmail.com>, Message-ID: <20180206221349.EAAF51C0B20@mail.domain2.com>, mail_id: m63tVFnrkJA4, Hits: 1.307, size: 6742, queued_as: A7A291C0B1C, 659 ms, Tests: [HTML_IMAGE_ONLY_16=1.048,HTML_MESSAGE=0.001,HTML_SHORT_LINK_IMG_2=0.259,NO_RELAYS=-0.001]
Feb  6 23:13:50 mail postfix/amavis/smtp[11929]: 0A63C1C0B1F: to=<my-gmail-account@gmail.com>, relay=127.0.0.1[127.0.0.1]:10024, delay=0.77, delays=0.07/0/0/0.7, dsn=2.0.0, status=sent (250 2.0.0 from MTA(smtp:[127.0.0.1]:10025): 250 2.0.0 Ok: queued as A7A291C0B1C)
Feb  6 23:13:50 mail postfix/qmgr[5093]: 0A63C1C0B1F: removed
Feb  6 23:13:50 mail postfix/smtp[11935]: Untrusted TLS connection established to gmail-smtp-in.l.google.com[2a00:1450:400c:c07::1b]:25: TLSv1.2 with cipher ECDHE-RSA-AES128-GCM-SHA256 (128/128 bits)
Feb  6 23:13:51 mail postfix/smtp[11935]: A7A291C0B1C: to=<my-gmail-account@gmail.com>, relay=gmail-smtp-in.l.google.com[2a00:1450:400c:c07::1b]:25, delay=0.45, delays=0.05/0/0.21/0.18, dsn=2.0.0, status=sent (250 2.0.0 OK 1517955231 v5si264916wmg.171 - gsmtp)
Feb  6 23:13:51 mail postfix/qmgr[5093]: A7A291C0B1C: removed

Postfix config
# --------------------
# INSTALL-TIME CONFIGURATION INFORMATION
#
# location of the Postfix queue. Default is /var/spool/postfix.
queue_directory = /var/spool/postfix

# location of all postXXX commands. Default is /usr/sbin.
command_directory = /usr/sbin

# location of all Postfix daemon programs (i.e. programs listed in the
# master.cf file). This directory must be owned by root.
# Default is /usr/libexec/postfix
daemon_directory = /usr/lib/postfix/sbin

# location of Postfix-writable data files (caches, random numbers).
# This directory must be owned by the mail_owner account (see below).
# Default is /var/lib/postfix.
data_directory = /var/lib/postfix

# owner of the Postfix queue and of most Postfix daemon processes.
# Specify the name of a user account THAT DOES NOT SHARE ITS USER OR GROUP ID
# WITH OTHER ACCOUNTS AND THAT OWNS NO OTHER FILES OR PROCESSES ON THE SYSTEM.
# In particular, don't specify nobody or daemon. PLEASE USE A DEDICATED USER.
# Default is postfix.
mail_owner = postfix

# The following parameters are used when installing a new Postfix version.
#
# sendmail_path: The full pathname of the Postfix sendmail command.
# This is the Sendmail-compatible mail posting interface.
#
sendmail_path = /usr/sbin/sendmail

# newaliases_path: The full pathname of the Postfix newaliases command.
# This is the Sendmail-compatible command to build alias databases.
#
newaliases_path = /usr/bin/newaliases

# full pathname of the Postfix mailq command.  This is the Sendmail-compatible
# mail queue listing command.
mailq_path = /usr/bin/mailq

# group for mail submission and queue management commands.
# This must be a group name with a numerical group ID that is not shared with
# other accounts, not even with the Postfix account.
setgid_group = postdrop

# external command that is executed when a Postfix daemon program is run with
# the -D option.
#
# Use "command .. & sleep 5" so that the debugger can attach before
# the process marches on. If you use an X-based debugger, be sure to
# set up your XAUTHORITY environment variable before starting Postfix.
#
debugger_command =
    PATH=/bin:/usr/bin:/usr/local/bin:/usr/X11R6/bin
    ddd $daemon_directory/$process_name $process_id & sleep 5

debug_peer_level = 2

# --------------------
# CUSTOM SETTINGS
#

# SMTP server response code when recipient or domain not found.
unknown_local_recipient_reject_code = 550

# Do not notify local user.
biff = no

# Disable the rewriting of "site!user" into "user@site".
swap_bangpath = no

# Disable the rewriting of the form "user%domain" to "user@domain".
allow_percent_hack = no

# Allow recipient address start with '-'.
allow_min_user = no

# Disable the SMTP VRFY command. This stops some techniques used to
# harvest email addresses.
disable_vrfy_command = yes

# Enable both IPv4 and/or IPv6: ipv4, ipv6, all.
inet_protocols = all

# Enable all network interfaces.
inet_interfaces = all

#
# TLS settings.
#
# SSL key, certificate, CA
#
smtpd_tls_key_file = /etc/ssl/private/iRedMail.key
smtpd_tls_cert_file = /etc/ssl/certs/iRedMail.crt
smtpd_tls_CAfile = /etc/ssl/certs/iRedMail.crt

#
# Disable SSLv2, SSLv3
#
smtpd_tls_protocols = !SSLv2 !SSLv3
smtpd_tls_mandatory_protocols = !SSLv2 !SSLv3
smtp_tls_protocols = !SSLv2 !SSLv3
smtp_tls_mandatory_protocols = !SSLv2 !SSLv3
lmtp_tls_protocols = !SSLv2 !SSLv3
lmtp_tls_mandatory_protocols = !SSLv2 !SSLv3

#
# Fix 'The Logjam Attack'.
#
smtpd_tls_exclude_ciphers = aNULL, eNULL, EXPORT, DES, RC4, MD5, PSK, aECDH, EDH-DSS-DES-CBC3-SHA, EDH-RSA-DES-CDC3-SHA, KRB5-DE5, CBC3-SHA
smtpd_tls_dh512_param_file = /etc/ssl/dh512_param.pem
smtpd_tls_dh1024_param_file = /etc/ssl/dh2048_param.pem

tls_random_source = dev:/dev/urandom

# Log only a summary message on TLS handshake completion — no logging of client
# certificate trust-chain verification errors if client certificate
# verification is not required. With Postfix 2.8 and earlier, log the summary
# message, peer certificate summary information and unconditionally log
# trust-chain verification errors.
smtp_tls_loglevel = 1
smtpd_tls_loglevel = 1

# Opportunistic TLS: announce STARTTLS support to remote SMTP clients, but do
# not require that clients use TLS encryption.
smtpd_tls_security_level = may

# Produce `Received:` message headers that include information about the
# protocol and cipher used, as well as the remote SMTP client CommonName and
# client certificate issuer CommonName.
# This is disabled by default, as the information may be modified in transit
# through other mail servers. Only information that was recorded by the final
# destination can be trusted.
#smtpd_tls_received_header = yes

# Opportunistic TLS, used when Postfix sends email to remote SMTP server.
# Use TLS if this is supported by the remote SMTP server, otherwise use
# plaintext.
# References:
#   - http://www.postfix.org/TLS_README.html#client_tls_may
#   - http://www.postfix.org/postconf.5.html#smtp_tls_security_level
smtp_tls_security_level = may

# Use the same CA file as smtpd.
smtp_tls_CAfile = $smtpd_tls_CAfile
smtp_tls_note_starttls_offer = yes

# Enable long, non-repeating, queue IDs (queue file names).
# The benefit of non-repeating names is simpler logfile analysis and easier
# queue migration (there is no need to run "postsuper" to change queue file
# names that don't match their message file inode number).
#enable_long_queue_ids = yes

# Reject unlisted sender and recipient
smtpd_reject_unlisted_recipient = yes
smtpd_reject_unlisted_sender = yes

# Header and body checks with PCRE table
header_checks = pcre:/etc/postfix/header_checks
body_checks = pcre:/etc/postfix/body_checks.pcre

# A mechanism to transform commands from remote SMTP clients.
# This is a last-resort tool to work around client commands that break
# interoperability with the Postfix SMTP server. Other uses involve fault
# injection to test Postfix's handling of invalid commands.
# Requires Postfix-2.7+.
#smtpd_command_filter = pcre:/etc/postfix/command_filter.pcre

# HELO restriction
smtpd_helo_required = yes
smtpd_helo_restrictions =
    permit_mynetworks
    permit_sasl_authenticated
    check_helo_access pcre:/etc/postfix/helo_access.pcre
    reject_non_fqdn_helo_hostname
    reject_unknown_helo_hostname

# Sender restrictions
smtpd_sender_restrictions =
    reject_unknown_sender_domain
    reject_non_fqdn_sender
    reject_unlisted_sender
    permit_mynetworks
    permit_sasl_authenticated
    check_sender_access pcre:/etc/postfix/sender_access.pcre

# Recipient restrictions
smtpd_recipient_restrictions =
    reject_unknown_recipient_domain
    reject_non_fqdn_recipient
    reject_unlisted_recipient
    check_policy_service inet:127.0.0.1:7777
    permit_mynetworks
    permit_sasl_authenticated
    reject_unauth_destination

# END-OF-MESSAGE restrictions
smtpd_end_of_data_restrictions =
    check_policy_service inet:127.0.0.1:7777

# Data restrictions
smtpd_data_restrictions = reject_unauth_pipelining

proxy_read_maps = $canonical_maps $lmtp_generic_maps $local_recipient_maps $mydestination $mynetworks $recipient_bcc_maps $recipient_canonical_maps $relay_domains $relay_recipient_maps $relocated_maps $sender_bcc_maps $sender_canonical_maps $smtp_generic_maps $smtpd_sender_login_maps $transport_maps $virtual_alias_domains $virtual_alias_maps $virtual_mailbox_domains $virtual_mailbox_maps $smtpd_sender_restrictions $sender_dependent_relayhost_maps

# Avoid duplicate recipient messages. Default is 'yes'.
enable_original_recipient = no

# Virtual support.
virtual_minimum_uid = 2000
virtual_uid_maps = static:2000
virtual_gid_maps = static:2000
virtual_mailbox_base = /storage/vmail

# Do not set virtual_alias_domains.
virtual_alias_domains =

#
# Enable SASL authentication on port 25 and force TLS-encrypted SASL authentication.
# WARNING: NOT RECOMMENDED to enable smtp auth on port 25, all end users should
#          be forced to submit email through port 587 instead.
#
smtpd_sasl_auth_enable = yes
smtpd_sasl_security_options = noanonymous
smtpd_tls_auth_only = yes

# hostname
myhostname = mail.domain1.com
myorigin = mail.domain1.com
mydomain = mail.domain1.com

# trusted SMTP clients which are allowed to relay mail through Postfix.
#
# Note: additional IP addresses/networks listed in mynetworks should be listed
#       in iRedAPD setting 'MYNETWORKS' (in `/opt/iredapd/settings.py`) too.
#       for example:
#
#       MYNETWORKS = ['xx.xx.xx.xx', 'xx.xx.xx.0/24', ...]
#
mynetworks = SERVER_PUBLIC_IP 127.0.0.0/8 [::1]

# Accepted local emails
mydestination = $myhostname, localhost, localhost.localdomain

alias_maps = hash:/etc/postfix/aliases
alias_database = hash:/etc/postfix/aliases

# Default message_size_limit.
message_size_limit = 15728640

# The set of characters that can separate a user name from its extension
# (example: user+foo), or a .forward file name from its extension (example:
# .forward+foo).
# Postfix 2.11 and later supports multiple characters.
recipient_delimiter = +

# The time after which the sender receives a copy of the message headers of
# mail that is still queued. Default setting is disabled (0h) by Postfix.
#delay_warning_time = 1h
compatibility_level = 2
#
# Lookup virtual mail accounts
#
transport_maps =
    proxy:mysql:/etc/postfix/mysql/transport_maps_user.cf
    proxy:mysql:/etc/postfix/mysql/transport_maps_domain.cf

sender_dependent_relayhost_maps =
    proxy:mysql:/etc/postfix/mysql/sender_dependent_relayhost_maps.cf

# Lookup table with the SASL login names that own the sender (MAIL FROM) addresses.
smtpd_sender_login_maps =
    proxy:mysql:/etc/postfix/mysql/sender_login_maps.cf

virtual_mailbox_domains =
    proxy:mysql:/etc/postfix/mysql/virtual_mailbox_domains.cf

relay_domains =
    $mydestination
    proxy:mysql:/etc/postfix/mysql/relay_domains.cf

virtual_mailbox_maps =
    proxy:mysql:/etc/postfix/mysql/virtual_mailbox_maps.cf

virtual_alias_maps =
    proxy:mysql:/etc/postfix/mysql/virtual_alias_maps.cf
    proxy:mysql:/etc/postfix/mysql/domain_alias_maps.cf
    proxy:mysql:/etc/postfix/mysql/catchall_maps.cf
    proxy:mysql:/etc/postfix/mysql/domain_alias_catchall_maps.cf

sender_bcc_maps =
    proxy:mysql:/etc/postfix/mysql/sender_bcc_maps_user.cf
    proxy:mysql:/etc/postfix/mysql/sender_bcc_maps_domain.cf

recipient_bcc_maps =
    proxy:mysql:/etc/postfix/mysql/recipient_bcc_maps_user.cf
    proxy:mysql:/etc/postfix/mysql/recipient_bcc_maps_domain.cf

#
# Postscreen
#
postscreen_greet_action = enforce
postscreen_blacklist_action = enforce
postscreen_dnsbl_action = enforce
postscreen_dnsbl_threshold = 2
postscreen_dnsbl_sites =
    zen.spamhaus.org=127.0.0.[2..11]*3
    b.barracudacentral.org=127.0.0.[2..11]*2

postscreen_dnsbl_reply_map = texthash:/etc/postfix/postscreen_dnsbl_reply
postscreen_access_list = permit_mynetworks cidr:/etc/postfix/postscreen_access.cidr

# Require Postfix-2.11+
postscreen_dnsbl_whitelist_threshold = -2
#
# Dovecot SASL support.
#
smtpd_sasl_type = dovecot
smtpd_sasl_path = private/dovecot-auth
virtual_transport = dovecot
dovecot_destination_recipient_limit = 1

#
# Amavisd + SpamAssassin + ClamAV
#
content_filter = smtp-amavis:[127.0.0.1]:10024

# Concurrency per recipient limit.
smtp-amavis_destination_recipient_limit = 1

Do you have any idea why from one account I got this error?

----

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2

Re: Sender address rejected, please authenticate (in reply to RCPT TO com)

*) Do you have same domain on both sender server and recipient server?
*) Or, the sender domain is hosted on the relay server but you send email without smtp authentication?

3

Re: Sender address rejected, please authenticate (in reply to RCPT TO com)

Thanks for quick reply. I think you show me a possible reason of that.

domain2.com was earlier mailbox configured at the same provider as external-mail-server.com.
The dns of this provider has still MX records for old mailbox configuration and probably when I sending mail to mailbox of this provider it looks first in local dns and found old MX records.

4

Re: Sender address rejected, please authenticate (in reply to RCPT TO com)

It's not about DNS records. Is "domain2.com" a mail domain hosted on both servers?