First off a big thank you to Matt Messmer for the fix.
Open your mail log
open /var/log/mail.log Open the file /etc/postfix/main.cf in any text editor.
Add this to main.cf
myorigin = gmail.com myhostname = smtp.gmail.com relayhost = [smtp.gmail.com]:587 smtp_sasl_auth_enable = yes smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd smtp_sasl_security_options = noanonymous smtp_sasl_mechanism_filter = plain inet_protocols = ipv4 smtp_use_tls = yes smtp_tls_security_level=encrypt tls_random_source=dev:/dev/urandom
I had to comment these out for mine to work
#mydomain_fallback = e4ed8caa87.nxcli.net #sender_canonical_maps = regexp:/etc/postfix/sender_canonical #recipient_canonical_maps = regexp:/etc/postfix/recipient_canonical
Open /private/etc/postfix/master.cf
Uncomment this line (remove the #) tlsmgr unix - - n - 1 tlsmgr
Create sasl_passwd
sudo nano /etc/postfix/sasl_passwd
add this line to it
[smtp.gmail.com]:587 username@gmail.com:password CMD-X to close Y to save NOTE: Change username and password to your google username and password
Run the following commands in terminal, one by one
sudo chmod 600 /etc/postfix/sasl_passwd sudo postmap /etc/postfix/sasl_passwd sudo launchctl stop org.postfix.master sudo launchctl start org.postfix.master sudo postfix upgrade-configuration sudo postfix reload sudo postfix flush
Testing
date | mail -s test username@gmail.com
Troubleshooting
Pay close attention to mail.log along the way, note the errors and fix them.