SENDMAIL on MAC OSX Yosemite http://www.garron.me/en/mac/postfix-relay-gmail-mac-os-x-local-smtp.html Create a file to store our credentials: sudo vim /etc/postfix/sasl_passwd Add something like this: smtp.gmail.com:587 [email protected]:password Now run: sudo postmap /etc/postfix/sasl_passwd Prepare the postfix main config file: sudo vim /etc/postfix/main.cf Add/update these lines relayhost=smtp.gmail.com:587 smtp_sasl_auth_enable=yes smtp_sasl_password_maps=hash:/etc/postfix/sasl_passwd smtp_use_tls=yes smtp_tls_security_level=encrypt tls_random_source=dev:/dev/urandom smtp_sasl_security_options = noanonymous smtp_always_send_ehlo = yes smtp_sasl_mechanism_filter = plain Stop/Start the service sudo postfix stop && sudo postfix start Check the queue for any errors mailq