Relay outbound email through GMail on OSX Mavericks

• Edit /etc/postfix/main.cf

################################
# GMail relay
###############################

# sets gmail as relay
relayhost = [smtp.gmail.com]:587

#  use tls
smtp_use_tls = yes

# use sasl when authenticating to foreign SMTP servers
smtp_sasl_auth_enable = yes

# path to password map file
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd

# eliminates default security options which are imcompatible with gmail
smtp_sasl_security_options =

smtp_tls_session_cache_database = btree:$data_directory/smtp_tls_session_cache

• Create and edit /etc/postfix/sasl_passwd (Create an app specific password if you use Google 2-factor authentication for GMail)

[smtp.gmail.com]:587  username:password

• Generate sasl_passwd files

sudo postmap /etc/postfix/sasl_passwd

• Reload Postfix

sudo postfix reload

• Send test email to yourself

date | mail -s testing your@email.com

• Debug

tail -f /var/log/mail.log