I have Postfix up and working perfect. It receives and sends email fine with no TLS and SASL but I installed Dovecot and then generated some self signed certificates using 'openssl' and for some reason I can't send from my IMAP server. I get this in my logs: Code: Mar 3 11:20:45 mail dovecot: imap-login: Login: user=<carlos>, method=PLAIN, rip=10.1.1.204, lip=192.168.0.200, TLS Mar 3 11:21:20 mail postfix/smtpd[1386]: connect from tuna.mydomain.tld[10.1.1.204] Mar 3 11:21:20 mail postfix/smtpd[1386]: setting up TLS connection from tuna.mydomain.tld[10.1.1.204] Mar 3 11:21:20 mail postfix/smtpd[1386]: SSL_accept error from tuna.mydomain.tld[10.1.1.204]: 0 Mar 3 11:21:20 mail postfix/smtpd[1386]: warning: TLS library problem: 1386:error:14094418:SSL routines:SSL3_READ_BYTES:tlsv1 alert unknown ca:s3_pkt.c:1061:SSL alert number 48: Mar 3 11:21:20 mail postfix/smtpd[1386]: lost connection after STARTTLS from tuna.mydomain.tld[10.1.1.204] Mar 3 11:21:20 mail postfix/smtpd[1386]: disconnect from tuna.mydomain.tld[10.1.1.204] Does anyone know what could be causing this issue? I don't show any other errors in my logs but I am watching them over and over. Postfix receives mail perfect and I can send in plain text with no TLS enabled. Below is my output of 'postconf -n': Code: alias_database = $alias_maps alias_maps = hash:/etc/postfix/aliases bounce_queue_lifetime = 1d command_directory = /usr/sbin config_directory = /etc/postfix daemon_directory = /usr/lib/postfix debug_peer_level = 2 delay_warning_time = 4h home_mailbox = mail/ html_directory = no inet_interfaces = all inet_protocols = ipv4 mail_owner = postfix mailq_path = /usr/bin/mailq manpage_directory = /usr/share/man mydestination = $myhostname, $mydomain, mail.$mydomain mydomain = iamunix.com myhostname = mail.iamunix.com mynetworks = $config_directory/mynetworks myorigin = $mydomain newaliases_path = /usr/bin/newaliases queue_directory = /var/spool/postfix readme_directory = no recipient_delimiter = + relayhost = sample_directory = /etc/postfix/sample sendmail_path = /usr/sbin/sendmail setgid_group = postdrop smtp_helo_timeout = 60s smtp_sasl_auth_enable = yes smtp_tls_session_cache_database = btree:/var/lib/postfix/smtp_scache smtpd_recipient_restrictions = permit_sasl_authenticated, permit_mynetworks, reject_unauth_destination, reject_non_fqdn_recipient, reject_unknown_recipient_domain, reject_non_fqdn_helo_hostname, reject_invalid_helo_hostname, reject_rbl_client zen.spamhaus.org, reject_rbl_client bl.spamcop.net, check_policy_service inet:127.0.0.1:10030 smtpd_sasl_auth_enable = yes smtpd_sasl_path = /var/run/dovecot/auth-client smtpd_sasl_security_options = noanonymous smtpd_sasl_type = dovecot smtpd_sender_restrictions = permit_sasl_authenticated, permit_mynetworks smtpd_tls_cert_file = /etc/ssl/certs/mail.crt smtpd_tls_key_file = /etc/ssl/private/mail.key smtpd_tls_loglevel = 1 smtpd_tls_session_cache_database = btree:/var/lib/postfix/smtpd_scache smtpd_use_tls = yes unknown_local_recipient_reject_code = 450