Postfix works fine with TLS on port 25, but when connecting on 465, it disconnects right away, and leaves this in the log file: Code: May 28 16:01:25 localhost postfix/smtpd[5735]: warning: connect to private/tlsmgr: Connection refused May 28 16:01:25 localhost postfix/smtpd[5735]: warning: problem talking to server private/tlsmgr: Connection refused May 28 16:01:26 localhost postfix/smtpd[5735]: warning: connect to private/tlsmgr: Connection refused May 28 16:01:26 localhost postfix/smtpd[5735]: warning: problem talking to server private/tlsmgr: Connection refused May 28 16:01:26 localhost postfix/smtpd[5735]: warning: no entropy for TLS key generation: disabling TLS support May 28 16:01:26 localhost postfix/smtpd[5735]: connect from localhost.localdomain[127.0.0.1] May 28 16:01:26 localhost postfix/smtpd[5735]: setting up TLS connection from localhost.localdomain[127.0.0.1] May 28 16:01:26 localhost postfix/smtpd[5735]: Could not allocate 'TLScontext->con' with SSL_new() May 28 16:01:26 localhost postfix/smtpd[5735]: warning: TLS library problem: 5735:error:140BA0C3:SSL routines:SSL_new:null ssl ctx:ssl_lib.c:231: May 28 16:01:26 localhost postfix/smtpd[5735]: lost connection after CONNECT from localhost.localdomain[127.0.0.1] May 28 16:01:26 localhost postfix/smtpd[5735]: disconnect from localhost.localdomain[127.0.0.1] master.cf has these important lines: Code: # only used by postfix-tls tlsmgr fifo - - n 300 1 tlsmgr smtps inet n - n - - smtpd -o smtpd_tls_wrappermode=yes -o smtpd_sasl_auth_enable=yes 587 inet n - n - - smtpd -o smtpd_enforce_tls=yes -o smtpd_sasl_auth_enable=yes