Dominic Simm

Using Mac OSX Lion command line mail with GMail as SMTP

I have been trying to get my command line mail working on my Mac OS X (Lion) today and I noticed that the normal postfix emails get treated as SPAM by Google and because I was sending emails to myself on my gmail account, that was an issue for me. So, I thought of using gmail as my outgoing SMTP server for this. Here are the steps I followed:

Configure Postfix for Gmail SMTP

Edit file /etc/postfix/

sudo vim /etc/postfix/

and add in the following below the commented out relay hosts

relayhost = []:587
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
smtp_sasl_security_options = noanonymous
smtp_use_tls = yes

Generate sasl_password if not already exists

sudo vim /etc/postfix/sasl_passwd

and enter in the following


Run the following commands

sudo chown root:wheel /etc/postfix/sasl_passwd
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

And you are done….

Now, you should be able to send emails from within the command line e.g. to send the contents of a directory as a tree to an email address

tree /var/www/somefolder | mail -s "contents"

Hope someone finds this useful!

[taken from]