Sample telnet: # telnet 127.0.0.1 25 Trying 127.0.0.1... Connected to 127.0.0.1. Escape character is '^]'. 220 mail.collect.org ESMTP Postfix helo test.test.com mail from me@test.com 530 5.7.0 Must issue a STARTTLS command first quit 221 2.0.0 Bye Connection closed by foreign host. sample maillog: Jul 30 10:47:16 64bit postfix/smtpd[23078]: connect from localhost[127.0.0.1] Jul 30 10:49:05 64bit postfix/smtpd[23078]: disconnect from localhost[127.0.0.1] relevant main.cf lines: smtp_use_tls = yes smtpd_use_tls = yes smtpd_enforce_tls = no smtp_tls_note_starttls_offer = yes smtpd_tls_key_file = /etc/postfix/ssl/smtpd.pem smtpd_tls_cert_file = /etc/postfix/ssl/smtpd.pem smtpd_tls_CAfile = /etc/postfix/ssl/smtpd.pem smtpd_tls_loglevel =3 smtpd_tls_received_header = yes smtpd_tls_session_cache_timeout = 3600s tls_random_source = dev:/dev/urandom smtpd_sasl_auth_enable = yes smtp_sasl_type = cyrus smtpd_recipient_restrictions = permit_mynetworks, permit_sasl_authenticated, reject_unknown_recipient_domain, reject_unauth_destination smtpd_helo_required = yes smtpd_helo_restrictions = permit_mynetworks, permit_sasl_authenticated, reject_invalid_hostname, reject_non_fqdn_hostname, reject_unknown_hostname smtp_client_restrictions = permit_mynetworks, permit_sasl_authenticated, reject_maps_rbl, reject_unknown_client smtpd_sender_restrictions = reject_unknown_sender_domain smtpd_sasl_security_options = noanonymous broken_sasl_auth_clients = yes