sendmail help

[Frank Ianella]

i am trying to use the sendmail applet to relay to smtp.gmail.com but
cannot figure out the neccessary command syntax.

using s_client with base64 encoded user:pass and the correct ca cert i
can authenticate fine. i just can seem to do it via sendmail.

an strace on './sendmail -S smtp.gmail.com:587 -f user at gmail.com'
shows the server requireing the starttls command but how to supply it.

./sendmail -H "openssl s_client -crlf -starttls smtp -connect
smtp.gmail.com:587 \
-CApath /etc/ssl/certs" -f user at gmail.com

the above also fails with 'sendmail: INIT failed' which according to
sendmail.c means sendmail did not receive a 250. again not sure.

any help is appreciated