I made the server certificates from instructions at http://postfix.state-of-mind.de/patrick.koetter/smtpauth/postfix_tls_support.html and I got some inspirations from http://souptonuts.sourceforge.net/postfix_tutorial.html Oct 11 00:15:17 david-laptop postfix/smtpd[8395]: idle timeout -- exiting Oct 11 00:17:24 david-laptop postfix/pickup[8393]: 3AEB424675D: uid=1000 from= Oct 11 00:17:24 david-laptop postfix/cleanup[8421]: 3AEB424675D: message-id=<20081010231724.3AEB424675D@david-laptop.davidroderick.co.uk> Oct 11 00:17:24 david-laptop postfix/qmgr[8392]: 3AEB424675D: from=, size=411, nrcpt=1 (queue active) Oct 11 00:17:27 david-laptop postfix/smtp[8423]: certificate verification failed for smtp.gmail.com[209.85.135.109]:587: untrusted issuer /C=ZA/ST=Western Cape/L=Cape Town/O=Thawte Consulting cc/OU=Certification Services Division/CN=Thawte Premium Server CA/emailAddress=premium-server@thawte.com Oct 11 00:17:28 david-laptop postfix/smtp[8423]: 3AEB424675D: to=, relay=smtp.gmail.com[209.85.135.109]:587, delay=4.7, delays=0.03/0.15/4/0.54, dsn=5.5.1, status=bounced (host smtp.gmail.com[209.85.135.109] said: 530-5.5.1 Authentication Required. Learn more at 530 5.5.1 http://mail.google.com/support/bin/answer.py?answer=14257 y6sm9694020mug.7 (in reply to MAIL FROM command)) Oct 11 00:17:29 david-laptop postfix/cleanup[8421]: 6E4C824675E: message-id=<20081010231729.6E4C824675E@david-laptop.davidroderick.co.uk> Oct 11 00:17:29 david-laptop postfix/bounce[8427]: 3AEB424675D: sender non-delivery notification: 6E4C824675E Oct 11 00:17:29 david-laptop postfix/qmgr[8392]: 6E4C824675E: from=<>, size=2684, nrcpt=1 (queue active) Oct 11 00:17:29 david-laptop postfix/qmgr[8392]: 3AEB424675D: removed Oct 11 00:17:29 david-laptop postfix/local[8428]: 6E4C824675E: to=, relay=local, delay=0.02, delays=0.01/0.01/0/0, dsn=2.0.0, status=sent (delivered to mailbox) Oct 11 00:17:29 david-laptop postfix/qmgr[8392]: 6E4C824675E: removed david@david-laptop:/etc/postfix:565$ david@david-laptop:/etc/postfix:565$ telnet localhost 25 Trying 127.0.0.1... Connected to localhost. Escape character is '^]'. 220 david-laptop.davidroderick.co.uk ESMTP Postfix (Ubuntu) EHLO u 250-david-laptop.davidroderick.co.uk 250-PIPELINING 250-SIZE 10240000 250-VRFY 250-ETRN 250-ENHANCEDSTATUSCODES 250-8BITMIME 250 DSN STARTTLS 502 5.5.1 Error: command not implemented ############### # See /usr/share/postfix/main.cf.dist for a commented, more complete version mydomain = davidroderick.co.uk myhostname = david-laptop.davidroderick.co.uk mynetworks = localhost alias_maps = hash:/etc/aliases alias_database = hash:/etc/aliases # Debian specific: Specifying a file name will cause the first # line of that file to be used as the name. The Debian default # is /etc/mailname. #myorigin = /etc/mailname smtpd_banner = $myhostname ESMTP $mail_name (Ubuntu) biff = no # appending .domain is the MUA's job. append_dot_mydomain = no # Uncomment the next line to generate "delayed mail" warnings #delay_warning_time = 4h readme_directory = no inet_interfaces = localhost mynetworks_style = locallost mynetworks_style = subnet relayhost = [smtp.gmail.com]:587 smtp_sasl_auth_enable = yes smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd smtp_sasl_security_options = smtp_use_tls = yes #smtpd_tls_auth_only = yes smtpd_tls_CApath = /etc/postfix/certs smtpd_tls_key_file = /etc/postfix/newreq.pem smtpd_tls_cert_file = /etc/postfix/newcert.pem smtpd_tls_CAfile = /etc/postfix/cacert.pem smtpd_tls_loglevel = 3 smtpd_tls_received_header = yes smtpd_tls_session_cache_timeout = 3600s tls_random_source = dev:/dev/urandom ############ ## Add these lines to the bottom on main.cf ## ## ## TLS Settings # # For no logs set = 0 # smtp_tls_loglevel = 1 # # smtp_enforce_tls = yes # Above is commented because doing it site by site below smtp_tls_per_site = hash:/etc/postfix/tls_per_site # smtp_tls_CAfile = /etc/postfix/cacert.pem smtp_tls_cert_file = /etc/postfix/FOO-cert.pem smtp_tls_key_file = /etc/postfix/FOO-key.pem smtp_tls_session_cache_database = btree:/var/run/smtp_tls_session_cache smtp_use_tls = yes smtpd_tls_session_cache_database = btree:/var/run/smtpd_tls_session_cache smtpd_use_tls = yes ## SASL Settings # # This is going in to THIS server # smtpd_sasl_auth_enable = no # # We need this # smtp_sasl_auth_enable = yes # smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd # smtpd_sasl_local_domain = $myhostname # smtp_sasl_security_options = noanonymous # #smtp_sasl_security_options = # smtp_sasl_tls_security_options = noanonymous # smtpd_sasl_application_name = smtpd ## Gmail Relay # relayhost = [smtp.gmail.com] ## Good for Testing # sender_bcc_maps = hash:/etc/postfix/bcc_table # Disable DNS Lookups disable_dns_lookups = yes # # Great New feature Address Mapping # for example may mchirico@localhost to mchirico@gmail.com smtp_generic_maps = hash:/etc/postfix/generic # # transport_maps = hash:/etc/postfix/transport