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I configured postfix with ssl/tls. and created an smtp. However I am unable to send test email and/or login.

"Text below first defines error log (different attempts) and then configuration files."

Error log on terminal.

[First Attempt]
[root@domain postfix]# telnet mail.example.org 587
Trying 139.59.182.62...
Connected to mail.example.org.
Escape character is '^]'.
220 example.org ESMTP Postfix
ehlo mail.example.org
250-example.org
250-PIPELINING
250-SIZE 10240000
250-VRFY
250-ETRN
250-STARTTLS
250-AUTH PLAIN
250-AUTH=PLAIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN
starttls
220 2.0.0 Ready to start TLS
ehlo mail.example.org
Connection closed by foreign host.

[Second Attempt]
[root@domain postfix]# telnet mail.example.org 587
Trying 139.59.182.62...
Connected to mail.example.org.
Escape character is '^]'.
220 example.org ESMTP Postfix
ehlo mail.example.org
250-example.org
250-PIPELINING
250-SIZE 10240000
250-VRFY
250-ETRN
250-STARTTLS
250-AUTH PLAIN
250-AUTH=PLAIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN
auth plain
334
username
535 5.7.8 Error: authentication failed: another step is needed in     authentication
quit
221 2.0.0 Bye
Connection closed by foreign host.

[Third Attempt]
[root@domain postfix]# telnet mail.example.org 587
Trying 139.59.182.62...
Connected to mail.example.org.
Escape character is '^]'.
220 example.org ESMTP Postfix
ehlo mail.example.org
250-example.org
250-PIPELINING
250-SIZE 10240000
250-VRFY
250-ETRN
250-STARTTLS
250-AUTH PLAIN
250-AUTH=PLAIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN
MAIL FROM:<user@domain.org>
250 2.1.0 Ok
RCPT TO:<******@gmail.com>
454 4.7.1 <*******@gmail.com>: Relay access denied
quit
221 2.0.0 Bye
Connection closed by foreign host.

/var/log/maillog file

Aug 26 19:55:11 example postfix/smtpd[22132]: connect from example.org[00.00.00.00]
Aug 26 19:55:22 example postfix/smtpd[22132]: warning: example.org[00.00.00.00]: SASL plain authentication failed: another step is needed in authentication
Aug 26 19:55:40 example postfix/smtpd[22132]: disconnect from example.org[00.00.00.00]
Aug 26 19:55:42 example postfix/smtpd[22132]: connect from example.org[00.00.00.00]
Aug 26 19:56:25 example postfix/smtpd[22132]: NOQUEUE: reject: RCPT from example.org[00.00.00.00]: 454 4.7.1 <*******@gmail.com>: Relay access denied; from=<******@example.org> to=<*******@gmail.com> proto=ESMTP helo=<mail.domain.org>
Aug 26 19:56:30 example postfix/smtpd[22132]: disconnect from example.org[00.00.00.00]
Aug 26 19:59:50 example postfix/anvil[22134]: statistics: max connection rate 2/60s for (submission:00.00.00.00) at Aug 26 19:55:11
Aug 26 19:59:50 example postfix/anvil[22134]: statistics: max connection count 1 for (submission:00.00.00.00) at Aug 26 19:54:29
Aug 26 19:59:50 example postfix/anvil[22134]: statistics: max cache size 1 at Aug 26 19:54:29  

Configuration files:

[main.cf]

 myorigin = domain1.org
 myhostname = domain2.org
 inet_protocols = all
 mydestination = mail.domain1.org, domain1
 relay_domains = domain2
 alias_maps = hash:/etc/aliases
 alias_database = hash:/etc/aliases
 alias_maps = hash:/etc/aliases
 alias_database = hash:/etc/aliases
 virtual_alias_domains = domain1.org domain2.org
 virtual_alias_maps = hash:/etc/postfix/virtual
 smtpd_use_tls = yes
 smtpd_tls_auth_only = no
 smtpd_tls_key_file = /etc/postfix/ssl/ssl.key
 smtpd_tls_cert_file = /etc/postfix/ssl/ssl.crt
 smtpd_tls_CAfile = /etc/postfix/ssl/interm.crt
 smtpd_tls_loglevel = 1
 smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
 smtp_sasl_security_options = noanonymous
 smtpd_tls_received_header = yes
 smtpd_tls_session_cache_timeout = 3600s
 tls_random_source = dev:/dev/urandom
 smtpd_sasl_auth_enable = yes
 smtp_sasl_auth_enable = yes
 smtpd_tls_protocols = !SSLv2, !SSLv3
 smtpd_sasl_local_domain =
 smtpd_delay_reject = yes
 broken_sasl_auth_clients = yes
 smtpd_recipient_restrictions =           reject_invalid_hostname,permit_sasl_authenticated,
    reject_unknown_recipient_domain,
    reject_unauth_destination,
    reject_rbl_client sbl.spamhaus.org,
    permit

 smtpd_helo_restrictions = reject_invalid_helo_hostname,
    reject_non_fqdn_helo_hostname,
    reject_unknown_helo_hostname
 mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
 mailbox_size_limit = 0
 recipient_delimiter = +
 inet_interfaces = all
 smtp_tls_security_level = may
 smtp_tls_note_starttls_offer = yes

[master.cf]

 smtp      inet  n       -       n       -       -       smtpd
 #smtp      inet  n       -       n       -       1       postscreen
 #smtpd     pass  -       -       n       -       -       smtpd
 #dnsblog   unix  -       -       n       -       0       dnsblog
 #tlsproxy  unix  -       -       n       -       0       tlsproxy
 submission inet n       -       n       -       -       smtpd
 #  -o syslog_name=postfix/submission
 #  -o smtpd_tls_security_level=encrypt
 #  -o smtpd_sasl_auth_enable=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=$mua_sender_restrictions
    -o smtpd_recipient_restrictions=permit_sasl_authenticated,reject
 #  -o milter_macro_daemon_name=ORIGINATING
 #smtps     inet  n       -       n       -       -       smtpd
 #  -o syslog_name=postfix/smtps     
 #  -o smtpd_tls_wrappermode=yes
 #  -o smtpd_sasl_auth_enable=yes
 #  -o smtpd_reject_unlisted_recipient=no
 #  -o smtpd_client_restrictions=$mua_client_restrictions
 #  -o smtpd_helo_restrictions=$mua_helo_restrictions
 #  -o smtpd_sender_restrictions=$mua_sender_restrictions
 #  -o smtpd_recipient_restrictions=permit_sasl_authenticated,reject
 #  -o milter_macro_daemon_name=ORIGINATING

if you need any details, please let me know. I am stuck at it. tried different ways, from different tutorials but didn't help much.

nix
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1 Answers1

2

Oh dear gods, don't attempt to negotiate TLS with telnet! You'd have to do the key exchange and all the other TLS functions by hand. That way lies madness. You're currently failing because ehlo mail.example.org is in no way an appropriate part of starttls.

If you want to test smtp starttls, use openssl specifically:
openssl s_client -connect <server>:587 -starttls smtp

84104
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