Thanks for the reply! I'm going crazy here.' I did change the setup between the set of logs in the previous e-mail. To keep things simple, I won't this time.
# postconf -n # shortened for relavent iformation biff = no broken_sasl_auth_clients = yes config_directory = /etc/postfix inet_interfaces = all local_recipient_maps = mydestination = mydomain = domain.com myhostname = real.domain.com mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128 mynetworks_style = host myorigin = $mydomain readme_directory = no recipient_delimiter = + smtp_helo_timeout = 60s smtp_tls_note_starttls_offer = yes smtpd_banner = Servee SMTP ESMTP smtpd_client_restrictions = reject_rbl_client sbl.spamhaus.org, reject_rbl_client blackholes.easynet.nl, reject_rbl_client dnsbl.njabl.org smtpd_data_restrictions = reject_unauth_pipelining smtpd_delay_reject = yes smtpd_hard_error_limit = 12 smtpd_helo_required = yes smtpd_helo_restrictions = warn_if_reject reject_non_fqdn_hostname, reject_invalid_hostname, permit smtpd_recipient_limit = 16 smtpd_recipient_restrictions = reject_unauth_pipelining, permit_mynetworks, permit_sasl_authenticated, reject_non_fqdn_recipient, reject_unknown_recipient_domain, reject_unauth_destination, check_policy_service inet:127.0.0.1:60000, permit smtpd_sasl_auth_enable = yes smtpd_sasl_authenticated_header = yes smtpd_sasl_local_domain = smtpd_sasl_path = /etc/postfix/sasl:/usr/lib/sasl2 smtpd_sasl_security_options = noanonymous smtpd_sender_restrictions = permit_sasl_authenticated, permit_mynetworks, warn_if_reject reject_non_fqdn_sender, reject_unknown_sender_domain, reject_unauth_pipelining, permit smtpd_soft_error_limit = 3 smtpd_tls_auth_only = no smtpd_tls_cert_file = /etc/postfix/postfix.cert smtpd_tls_key_file = /etc/postfix/postfix.key smtpd_tls_loglevel = 3 smtpd_tls_received_header = yes smtpd_tls_security_level = may smtpd_tls_session_cache_timeout = 3600s smtpd_use_tls = no tls_random_source = dev:/dev/urandom unknown_local_recipient_reject_code = 450 virtual_alias_maps = mysql:/etc/postfix/mysql_alias.cf virtual_gid_maps = mysql:/etc/postfix/mysql_gid.cf virtual_mailbox_base = /mnt/spool/mail/virtual virtual_mailbox_domains = mysql:/etc/postfix/mysql_domains.cf virtual_mailbox_maps = mysql:/etc/postfix/mysql_mailbox.cf virtual_uid_maps = mysql:/etc/postfix/mysql_uid.cf Here is the saslfinger output. # saslfinger -c saslfinger - postfix Cyrus sasl configuration Mon Oct 13 07:08:29 PDT 2008 version: 1.0.2 mode: client-side SMTP AUTH -- basics -- Postfix: 2.5.1 System: Ubuntu 8.04 \n \l -- smtp is linked to -- libsasl2.so.2 => /usr/lib/libsasl2.so.2 (0x00d68000) -- active SMTP AUTH and TLS parameters for smtp -- smtp_tls_note_starttls_offer = yes -- listing of /usr/lib/sasl2 -- total 792 drwxr-xr-x 2 root root 4096 2008-05-02 15:10 . drwxr-xr-x 55 root root 12288 2008-05-04 09:48 .. ... omitted ... *Cannot find the smtp_sasl_password_maps parameter in main.cf.* Client-side SMTP AUTH cannot work without this parameter! I'm using mysql, so I've included the #/etc/postfix/sasl/smtpd.conf pwcheck_method: auxprop auxprop_plugin: sql mech_list: login cram-md5 digest-md5 sql_engine: mysql sql_hostnames: localhost sql_user: mail sql_passwd: (password) sql_database: maildb sql_select: select clear from users where id='[EMAIL PROTECTED]' and enabled = 1 The above was also taken from the guide Master.cf smtp inet n - - - - smtpd submission inet n - - - - smtpd -o smtpd_sasl_auth_enable=yes # if you do not want to allow encryption only, comment out next line -o smtpd_tls_auth_only=yes -o smtpd_tls_security_level=encrypt # -o header_checks= # -o body_checks= -o smtpd_client_restrictions=permit_sasl_authenticated,reject_unauth_destination,reject -o smtpd_sasl_security_options=noanonymous,noplaintext -o smtpd_sasl_tls_security_options=noanonymous # -o milter_macro_daemon_name=ORIGINATING smtps inet n - - - - smtpd -o smtpd_tls_wrappermode=yes -o smtpd_sasl_auth_enable=yes -o smtpd_tls_auth_only=yes -o smtpd_client_restrictions=permit_sasl_authenticated,reject -o smtpd_sasl_security_options=noanonymous,noplaintext -o smtpd_sasl_tls_security_options=noanonymous # -o milter_macro_daemon_name=ORIGINATING Wit this setup, I'm getting in the log Oct 13 07:19:16 ec2-75-101-148-70 postfix/smtpd[9929]: connect from (outside host) Oct 13 07:19:16 ec2-75-101-148-70 postfix/smtpd[9929]: setting up TLS connection from (outside host) Oct 13 07:19:16 postfix/smtpd[9929]: SSL_accept error from (outside host): -1 Oct 13 07:19:16 postfix/smtpd[9929]: lost connection after STARTTLS from (outside host)