Postfix Using Gmail SMTP in Mac OSX Mavericks

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Configure Postfix for Gmail SMTP in Mac OSX Mavericks

Taken from Using MacOSX Lion command line mail with Gmail as SMTP

Edit file /etc/postfix/main.cf

sudo vim /etc/postfix/main.cf

and add in the following below the commented out relayhosts :-

myhostname = smtp.gmail.com

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# SASL SUPPORT FOR SERVERS
#
# The following options set parameters needed by Postfix to enable
# Cyrus-SASL support for authentication of mail servers.
#
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_use_tls = yes

Create a sasl_passwd if one doesn't exist

sudo vim /etc/postfix/sasl_passwd

and enter in the following:-

[smtp.gmail.com]:587 [email protected]:password

Run the following commands

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

test by sending the contents of a directory to an email address with the following:

tree /var/www/somefolder | mail -s "contents" [email protected]

If you receive the following error:

send-mail: fatal: chdir /Library/Server/Mail/Data/spool: No such file or directory

you can do the following:

sudo mkdir -p /Library/Server/Mail/Data/spool
sudo /usr/sbin/postfix set-permissions
sudo /usr/sbin/postfix start

as per this question.

NB: If things aint sending / receiving, and you're getting notices, check that the mail servers you're using are actually working!

NOTE: A crappy way to get around Google's

Someone just tried to sign in to your Google Account [youremail]@gmail.com from an app that doesn't meet modern security standards.

is to enable less secure apps on your account: https://www.google.com/settings/security/lesssecureapps. Do this at your own discretion.

this is not working. Close. I made some progress. But I am getting mailer daemons using the totally incorrect details here.
It is trying to send mail from [user]@smtp.gmail.com (where user is my mac username without the brackets)
I definitely setup my sasl_passwd, and I am using the email in the form of [account]@gmail.com:[password]
So, why it trying to send mail using my mac user @ smtp.gmail.com ? I think that may be the issue?? How do I fix this?

sudo nano /etc/postfix/main.cf

add below configs

mydomain_fallback = localhost
mail_owner = _postfix
setgid_group = _postdrop
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_use_tls = yes
#smtp_tls_security_level = encrypt
#tls_random_source = dev:/dev/urandom
smtp_sasl_mechanism_filter = login

in sasl_passwd

sudo nano /etc/postfix/sasl_passwd

smtp.gmail.com:587 [email protected]:password

then send email

date | mail -s test [email protected]

u will receive email from Google with subject "Review blocked sign-in attempt"
from the email you can activate the less secured apps

it works using macos sierra based on above config

hope it helps, as it took me nearly one hour to get it right.

Thank you @lvlaxpt. Adding this line: smtp_sasl_mechanism_filter = login in /etc/postfix/main.cf and restarting Postfix to commit the changes, fixed my issue on my macOS Sierra. :)

@lvlaxpt even with your config I am still receiving TLS is required, but our TLS engine is unavailable in mailq.

Nearly 4 hours later and 4am...and @n0mer you just solved my issue. Here is what I am running that seems to work:

myhostname = smtp.gmail.com
relayhost = [smtp.gmail.com]:587
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/private/etc/postfix/sasl_passwd
smtp_sasl_security_options = noanonymous
smtp_use_tls = yes
smtp_sasl_mechanism_filter = plain

i had issue that postfix is running,but when i send mail ,the username is the my mac username@smtp.gmail.com(i had in the sasl_passwd wrote the gmail username) ,then i got the ERROR 5.1.1,who can tell me how to deal with it