Hi, I am trying to get a CentOS 6 system relaying mail via my G-Mail account. I followed the instructions found at https://www.zulius.com/how-to/set-up-postfix-with-a-remote-smtp-relay-host/but there seems to be a problem with authentication. I have done some research but still can't get this working. Any suggestions ? It seems the user and password are correct. Dec 27 23:15:36 hbc postfix/pickup[2588]: 8DEB1410B3: uid=0 from=<root> Dec 27 23:15:36 hbc postfix/cleanup[2603]: 8DEB1410B3: message-id=< 20121227101536.8DEB1410B3 at hbc.hillcrest.org.nz> Dec 27 23:15:36 hbc postfix/qmgr[2589]: 8DEB1410B3: from=< root at hbc.hillcrest.org.nz>, size=317, nrcpt=1 (queue active) Dec 27 23:15:37 hbc postfix/smtp[2605]: connect to smtp.gmail.com[2607:f8b0:400e:c00::6d]:587: Network is unreachable Dec 27 23:15:37 hbc postfix/smtp[2605]: vstream_buf_get_ready: fd 15 got 45 Dec 27 23:15:37 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.109]:587: 220 mx.google.com ESMTP vo8sm17581810pbc.16 Dec 27 23:15:37 hbc postfix/smtp[2605]: > smtp.gmail.com[173.194.79.109]:587: EHLO hbc.hillcrest.org.nz Dec 27 23:15:37 hbc postfix/smtp[2605]: vstream_fflush_some: fd 15 flush 27 Dec 27 23:15:37 hbc postfix/smtp[2605]: vstream_buf_get_ready: fd 15 got 122 Dec 27 23:15:37 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.109]:587: 250-mx.google.com at your service, [121.75.4.39] Dec 27 23:15:37 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.109]:587: 250-SIZE 35882577 Dec 27 23:15:37 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.109]:587: 250-8BITMIME Dec 27 23:15:37 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.109]:587: 250-STARTTLS Dec 27 23:15:37 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.109]:587: 250 ENHANCEDSTATUSCODES Dec 27 23:15:37 hbc postfix/smtp[2605]: server features: 0x101b size 35882577 Dec 27 23:15:37 hbc postfix/smtp[2605]: > smtp.gmail.com[173.194.79.109]:587: STARTTLS Dec 27 23:15:37 hbc postfix/smtp[2605]: vstream_fflush_some: fd 15 flush 10 Dec 27 23:15:37 hbc postfix/smtp[2605]: vstream_buf_get_ready: fd 15 got 30 Dec 27 23:15:37 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.109]:587: 220 2.0.0 Ready to start TLS Dec 27 23:15:37 hbc postfix/smtp[2605]: event_request_timer: reset 0x7f79a9113bb0 0x7f79aa8429d0 5 Dec 27 23:15:37 hbc postfix/smtp[2605]: send attr request = seed Dec 27 23:15:37 hbc postfix/smtp[2605]: send attr size = 32 Dec 27 23:15:37 hbc postfix/smtp[2605]: vstream_fflush_some: fd 9 flush 22 Dec 27 23:15:37 hbc postfix/smtp[2605]: vstream_buf_get_ready: fd 9 got 60 Dec 27 23:15:37 hbc postfix/smtp[2605]: private/tlsmgr: wanted attribute: status Dec 27 23:15:37 hbc postfix/smtp[2605]: input attribute name: status Dec 27 23:15:37 hbc postfix/smtp[2605]: input attribute value: 0 Dec 27 23:15:37 hbc postfix/smtp[2605]: private/tlsmgr: wanted attribute: seed Dec 27 23:15:37 hbc postfix/smtp[2605]: input attribute name: seed Dec 27 23:15:37 hbc postfix/smtp[2605]: input attribute value: xIHq7bnC7bggzN5/v38KVLhUrfnowW/aYWlTcvBI1LM= Dec 27 23:15:37 hbc postfix/smtp[2605]: private/tlsmgr: wanted attribute: (list terminator) Dec 27 23:15:37 hbc postfix/smtp[2605]: input attribute name: (end) Dec 27 23:15:38 hbc postfix/smtp[2605]: > smtp.gmail.com[173.194.79.109]:587: EHLO hbc.hillcrest.org.nz Dec 27 23:15:38 hbc postfix/smtp[2605]: vstream_fflush_some: fd 15 flush 27 Dec 27 23:15:38 hbc postfix/smtp[2605]: vstream_buf_get_ready: fd 15 got 145 Dec 27 23:15:38 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.109]:587: 250-mx.google.com at your service, [121.75.4.39] Dec 27 23:15:38 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.109]:587: 250-SIZE 35882577 Dec 27 23:15:38 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.109]:587: 250-8BITMIME Dec 27 23:15:38 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.109]:587: 250-AUTH LOGIN PLAIN XOAUTH XOAUTH2 Dec 27 23:15:38 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.109]:587: 250 ENHANCEDSTATUSCODES Dec 27 23:15:38 hbc postfix/smtp[2605]: server features: 0x102b size 35882577 Dec 27 23:15:38 hbc postfix/smtp[2605]: maps_find: smtp_sasl_passwd: smtp.gmail.com: not found Dec 27 23:15:38 hbc postfix/smtp[2605]: maps_find: smtp_sasl_passwd: hash:/etc/postfix/sasl_passwd(0,lock|fold_fix): smtp.gmail.com:587 = clint.dilks at gmail.com: Dec 27 23:15:38 hbc postfix/smtp[2605]: smtp_sasl_passwd_lookup: host ` smtp.gmail.com' user `<user>@gmail.com' pass `<correct password>' Dec 27 23:15:38 hbc postfix/smtp[2605]: starting new SASL client Dec 27 23:15:38 hbc postfix/smtp[2605]: name_mask: noanonymous Dec 27 23:15:38 hbc postfix/smtp[2605]: smtp_sasl_authenticate: smtp.gmail.com[173.194.79.109]:587: SASL mechanisms LOGIN PLAIN XOAUTH XOAUTH2 Dec 27 23:15:38 hbc postfix/smtp[2605]: warning: SASL authentication failure: No worthy mechs found Dec 27 23:15:38 hbc postfix/smtp[2605]: 8DEB1410B3: SASL authentication failed; cannot authenticate to server smtp.gmail.com[173.194.79.109]: no mechanism available Dec 27 23:15:38 hbc postfix/smtp[2605]: > smtp.gmail.com[173.194.79.109]:587: QUIT Dec 27 23:15:38 hbc postfix/smtp[2605]: name_mask: resource Dec 27 23:15:38 hbc postfix/smtp[2605]: name_mask: software Dec 27 23:15:38 hbc postfix/smtp[2605]: vstream_fflush_some: fd 15 flush 6 Dec 27 23:15:38 hbc postfix/smtp[2605]: vstream_fflush_some: fd 15 flush 0 Dec 27 23:15:38 hbc postfix/smtp[2605]: disposing SASL state information Dec 27 23:15:39 hbc postfix/smtp[2605]: vstream_buf_get_ready: fd 15 got 45 Dec 27 23:15:39 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.108]:587: 220 mx.google.com ESMTP bi8sm14464509pab.15 Dec 27 23:15:39 hbc postfix/smtp[2605]: > smtp.gmail.com[173.194.79.108]:587: EHLO hbc.hillcrest.org.nz Dec 27 23:15:39 hbc postfix/smtp[2605]: vstream_fflush_some: fd 15 flush 27 Dec 27 23:15:39 hbc postfix/smtp[2605]: vstream_buf_get_ready: fd 15 got 122 Dec 27 23:15:39 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.108]:587: 250-mx.google.com at your service, [121.75.4.39] Dec 27 23:15:39 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.108]:587: 250-SIZE 35882577 Dec 27 23:15:39 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.108]:587: 250-8BITMIME Dec 27 23:15:39 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.108]:587: 250-STARTTLS Dec 27 23:15:39 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.108]:587: 250 ENHANCEDSTATUSCODES Dec 27 23:15:39 hbc postfix/smtp[2605]: server features: 0x101b size 35882577 Dec 27 23:15:39 hbc postfix/smtp[2605]: > smtp.gmail.com[173.194.79.108]:587: STARTTLS Dec 27 23:15:39 hbc postfix/smtp[2605]: vstream_fflush_some: fd 15 flush 10 Dec 27 23:15:39 hbc postfix/smtp[2605]: vstream_buf_get_ready: fd 15 got 30 Dec 27 23:15:39 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.108]:587: 220 2.0.0 Ready to start TLS Dec 27 23:15:39 hbc postfix/smtp[2605]: event_request_timer: reset 0x7f79a9113bb0 0x7f79aa8429d0 5 Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr request = seed Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr size = 32 Dec 27 23:15:39 hbc postfix/smtp[2605]: vstream_fflush_some: fd 9 flush 22 Dec 27 23:15:39 hbc postfix/smtp[2605]: vstream_buf_get_ready: fd 9 got 60 Dec 27 23:15:39 hbc postfix/smtp[2605]: private/tlsmgr: wanted attribute: status Dec 27 23:15:39 hbc postfix/smtp[2605]: input attribute name: status Dec 27 23:15:39 hbc postfix/smtp[2605]: input attribute value: 0 Dec 27 23:15:39 hbc postfix/smtp[2605]: private/tlsmgr: wanted attribute: seed Dec 27 23:15:39 hbc postfix/smtp[2605]: input attribute name: seed Dec 27 23:15:39 hbc postfix/smtp[2605]: input attribute value: Gvb7N21DayqKfDwTIIHM/2DY92tqdHFajB++bXjpXwE= Dec 27 23:15:39 hbc postfix/smtp[2605]: private/tlsmgr: wanted attribute: (list terminator) Dec 27 23:15:39 hbc postfix/smtp[2605]: input attribute name: (end) Dec 27 23:15:39 hbc postfix/smtp[2605]: > smtp.gmail.com[173.194.79.108]:587: EHLO hbc.hillcrest.org.nz Dec 27 23:15:39 hbc postfix/smtp[2605]: vstream_fflush_some: fd 15 flush 27 Dec 27 23:15:39 hbc postfix/smtp[2605]: vstream_buf_get_ready: fd 15 got 145 Dec 27 23:15:39 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.108]:587: 250-mx.google.com at your service, [121.75.4.39] Dec 27 23:15:39 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.108]:587: 250-SIZE 35882577 Dec 27 23:15:39 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.108]:587: 250-8BITMIME Dec 27 23:15:39 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.108]:587: 250-AUTH LOGIN PLAIN XOAUTH XOAUTH2 Dec 27 23:15:39 hbc postfix/smtp[2605]: < smtp.gmail.com[173.194.79.108]:587: 250 ENHANCEDSTATUSCODES Dec 27 23:15:39 hbc postfix/smtp[2605]: server features: 0x102b size 35882577 Dec 27 23:15:39 hbc postfix/smtp[2605]: maps_find: smtp_sasl_passwd: smtp.gmail.com: not found Dec 27 23:15:39 hbc postfix/smtp[2605]: maps_find: smtp_sasl_passwd: hash:/etc/postfix/sasl_passwd(0,lock|fold_fix): smtp.gmail.com:587 = <user>@ gmail.com:<correct password> Dec 27 23:15:39 hbc postfix/smtp[2605]: smtp_sasl_passwd_lookup: host ` smtp.gmail.com' user `' pass `' Dec 27 23:15:39 hbc postfix/smtp[2605]: starting new SASL client Dec 27 23:15:39 hbc postfix/smtp[2605]: name_mask: noanonymous Dec 27 23:15:39 hbc postfix/smtp[2605]: smtp_sasl_authenticate: smtp.gmail.com[173.194.79.108]:587: SASL mechanisms LOGIN PLAIN XOAUTH XOAUTH2 Dec 27 23:15:39 hbc postfix/smtp[2605]: warning: SASL authentication failure: No worthy mechs found Dec 27 23:15:39 hbc postfix/smtp[2605]: connect to subsystem private/defer Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr nrequest = 0 Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr flags = 0 Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr queue_id = 8DEB1410B3 Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr original_recipient = clint.dilks at gmail.com Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr recipient = clint.dilks at gmail.com Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr offset = 203 Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr dsn_orig_rcpt = Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr notify_flags = 0 Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr status = 4.7.0 Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr diag_type = x-sasl Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr diag_text = no mechanism available Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr mta_type = Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr mta_mname = Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr action = delayed Dec 27 23:15:39 hbc postfix/smtp[2605]: send attr reason = SASL authentication failed; cannot authenticate to server smtp.gmail.com[173.194.79.108]: no mechanism available Dec 27 23:15:39 hbc postfix/smtp[2605]: vstream_fflush_some: fd 16 flush 373 Dec 27 23:15:40 hbc postfix/smtp[2605]: vstream_buf_get_ready: fd 16 got 10 Dec 27 23:15:40 hbc postfix/smtp[2605]: private/defer socket: wanted attribute: status Dec 27 23:15:40 hbc postfix/smtp[2605]: input attribute name: status Dec 27 23:15:40 hbc postfix/smtp[2605]: input attribute value: 0 Dec 27 23:15:40 hbc postfix/smtp[2605]: private/defer socket: wanted attribute: (list terminator) Dec 27 23:15:40 hbc postfix/smtp[2605]: input attribute name: (end) Dec 27 23:15:40 hbc postfix/smtp[2605]: 8DEB1410B3: to=< clint.dilks at gmail.com>, relay=smtp.gmail.com[173.194.79.108]:587, delay=23, delays=20/0.04/3.3/0, dsn=4.7.0, status=deferred (SASL authentication failed; cannot authenticate to server smtp.gmail.com[173.194.79.108]: no mechanism available) Dec 27 23:15:40 hbc postfix/smtp[2605]: flush_add: site gmail.com id 8DEB1410B3 Dec 27 23:15:40 hbc postfix/smtp[2605]: match_hostname: gmail.com ~? hbc.hillcrest.org.nz Dec 27 23:15:40 hbc postfix/smtp[2605]: match_hostname: gmail.com ~? localhost.hillcrest.org.nz Dec 27 23:15:40 hbc postfix/smtp[2605]: match_hostname: gmail.com ~? localhost Dec 27 23:15:40 hbc postfix/smtp[2605]: match_list_match: gmail.com: no match Dec 27 23:15:40 hbc postfix/smtp[2605]: flush_add: site gmail.com id 8DEB1410B3 status 4 Dec 27 23:15:40 hbc postfix/smtp[2605]: > smtp.gmail.com[173.194.79.108]:587: QUIT Dec 27 23:15:40 hbc postfix/smtp[2605]: name_mask: resource Dec 27 23:15:40 hbc postfix/smtp[2605]: name_mask: software Dec 27 23:15:40 hbc postfix/smtp[2605]: vstream_fflush_some: fd 15 flush 6 Dec 27 23:15:40 hbc postfix/smtp[2605]: vstream_fflush_some: fd 15 flush 0 Dec 27 23:15:40 hbc postfix/smtp[2605]: disposing SASL state information My Postfix Config is currently alias_database = hash:/etc/aliases alias_maps = hash:/etc/aliases command_directory = /usr/sbin config_directory = /etc/postfix daemon_directory = /usr/libexec/postfix data_directory = /var/lib/postfix debug_peer_level = 3 debug_peer_list = smtp.gmail.com html_directory = no inet_interfaces = localhost inet_protocols = all mail_owner = postfix mailq_path = /usr/bin/mailq.postfix manpage_directory = /usr/share/man mydestination = $myhostname, localhost.$mydomain, localhost newaliases_path = /usr/bin/newaliases.postfix queue_directory = /var/spool/postfix readme_directory = /usr/share/doc/postfix-2.6.6/README_FILES relayhost = smtp.gmail.com:587 sample_directory = /usr/share/doc/postfix-2.6.6/samples sendmail_path = /usr/sbin/sendmail.postfix setgid_group = postdrop smtp_sasl_auth_enable = yes smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd smtp_sasl_security_options = noanonymous smtp_sasl_tls_security_options = noanonymous smtp_sasl_type = cyrus smtp_tls_CAfile = /etc/pki/tls/certs/ca-bundle.crt smtp_use_tls = yes smtpd_sasl_path = smtpd unknown_local_recipient_reject_code = 550 # rpm -qa | grep -i sasl cyrus-sasl-lib-2.1.23-13.el6_3.1.x86_64 cyrus-sasl-2.1.23-13.el6_3.1.x86_64 Any help appreciated :)