i have (tried to) configure postfix to relay mail to a gmail email account. Gmail requires ssl. i found through research tls == ssl. So i configured tls (and everything else for that matter) at http://souptonuts.sourceforge.net/postfix_tutorial.html. i continually get a handshake failure from smtp.gmail.com looking like this:
delivery via smtp.gmail.com[66.249.83.111]: Cannot start TLS: handshake failure

where do i look for success? to configure my certificates i created the following script (because i was doing it so much):

#remove all previous files
rm -rf FOO* demoCA &&
/etc/ssl/misc/CA.pl -newca &&
openssl req -new -nodes -keyout FOO-key.pem -out FOO-req.pem -days 3650 &&
openssl ca -out FOO-cert.pem -infiles FOO-req.pem &&
cp FOO-cert.pem FOO-key.pem demoCA/cacert.pem /etc/postfix &&
cp demoCA/cacert.pem /etc/postfix &&
chmod +644 /etc/postfix/FOO-cert.pem /etc/postfix/cacert.pem &&
chmod +400 /etc/postfix/FOO-key.pem &&
postfix reload &&
echo "success" ||
echo "failure"

and the tls part of main.cf looks like this:


#tls for smtp
smtp_enforce_tls = yes
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_recieved_header = yes
smtp_tls_session_cache_database = btree:/var/run/smtp_tls_session_cache
smtp_use_tls = yes

#tls for smtpd (which i don't even use!!!!!!!!!!!)
smtpd_tls_CAfile = /etc/postfix/cacert.pem
smtpd_tls_cert_file = /etc/postfix/FOO-cert.pem
smtpd_tls_key_file = /etc/postfix/FOO-key.pem
smtpd_tls_recieved_header = yes
smtpd_tls_session_cache_database = btree:/var/run/smtpd_tls_session_cache
smtpd_use_tls = yes

tls_random_source = dev:/dev/urandom

the rest of the added configuration follows the details in the above link...

thank you very much for *any* assistance in this matter