Ubuntu – Crontab and sSMTP

The easiest way to make sure the email that is sending with the correct name would be to run the cron job on the account you need it to send out:

Example

me@domain:~$ crontab -e

If you want the root user to send out the messages through mutt, try this one liner (it worked for me):

export EMAIL="Me <me@domain.com>" && mutt -s "subject" -a /home/user/directory/file*.xls -- user1@domain.com, user2@domain.com < /home/user/directory/message.txt

Hope this helps.

In the end I used sSMTP. It's far, far simpler than either Postfix or sendmail and does the job beautifully.

For future reference, here's how to use sSMTP with Yahoo Mail (don't worry, it's far less complex than it looks):

• Use Synaptic to download ssmtp. Alternatively you could run sudo apt-get install ssmtp.

• Open the config file at /etc/ssmtp/ssmtp.conf.

• Make the config look like this:

  root=[yourRealEmail@yahoo.com.au]
  mailhub=smtp.mail.yahoo.com:587
  FromLineOverride=YES
  UseSTARTTLS=YES
  AuthUser=[yourRealEmail@yahoo.com.au]
  AuthPass=[yourRealYahooPassword]
  TLS_CA_File=~/cert.pem
  

• Create the cert.pem file with OpenSSL. I used the command openssl req -x509 -newkey rsa:2048 -keyout key.pem -out cert.pem -days 9999 -nodes (more info at How to create a self-signed certificate with OpenSSL). You can stick the file anywhere, but I just chucked it in ~/. Wherever you put it, make sure you point the TLS_CA_File= line in ssmtp.conf to the correct location.

• Open the file /etc/ssmtp/revaliases and add the line:

  [yourPCUsername]:[yourRealEmail@yahoo.com.au]:smtp.mail.yahoo.com:587
  

  If you're running as root, I would think you need to add another line replacing your name with 'root'.

• That's it, you're good to go! To test, the easiest way (IMO) is to create a file with the following in it:

  To: [yourRealEmail@yahoo.com.au]
  From: "whateverYaWant" <[yourRealEmail@yahoo.com.au]>
  Subject: Some Notifying Email
  MIME-Version: 1.0
  Content-Type: text/plain
  
  Body of your email goes here! Hello world!
  

• Save and close the file, then to check you don't have the real sendmail installed, run sendmail -V - it should say 'sSMTP'.

• Finally, run cat fileWithEmailInIt.txt | sendmail -i -t, then wait a few seconds (10-30) and check your email!

Obviously, replace [yourRealEmail@yahoo.com.au] with your email (without the brackets) and [yourRealYahooPassword] with your Yahoo Mail password (again, without the brackets).

Additional note 1: If you have trouble with Gmail, try option 1 of this answer.
(Thanks to Ben Creasy!)

Additional note 2: If mail is sending from the command line but not through crontab, try changing FromLineOverride to NO in /etc/ssmtp/ssmtp.conf. You can also get more detailed logging by adding Debug=YES to ssmtp.conf - the extra logging goes to /var/log/mail.log.
(Thanks Jakub Kukul!)