How to send emails (with Gmail as SMTP server) from the cmdline when 2-Step Verification is ON

gmail_cmdline.md

Generate an App password for your Google account. Select the custom option from the drop-down menu. The password will work with any of the utilities below.

Compose, 'sendemail' with attachment

1. Install sendemail and dependencies

   sudo apt install libio-socket-ssl-perl libnet-ssleay-perl libterm-readkey-perl sendemail
   

2. Apply patch1 to simplify the mailing experience

   sudo patch /usr/bin/sendEmail < sendEmail-1.56-5.patch
   

3. Apply patch2 to add some colored confirmation when mail is sent

   sudo patch /usr/bin/sendEmail < sendEmail-1.56-5_color.patch
   

4. Add the following alias in your shell's rc file

   alias mail='sendemail -f yourmail@gmail.com -s smtp.gmail.com:587 -o tls=yes -xu yourmail -t '
   

5. Send a mail with 2 attachments

   mail johndoe@somedomain.com -a attachment1.pdf attachment2.mp3
   

Send emails using ssmtp

1. Install ssmtp

   sudo apt install ssmtp
   

2. Configure ssmtp (/etc/ssmtp/ssmtp.conf)

root=yourmail@gmail.com
mailhub=smtp.gmail.com:465
FromLineOverride=YES
AuthUser=yourmail@gmail.com
AuthPass=generated_app_password
UseTLS=YES

3. Send mails from the cmdline

Send attachments using mpack

mpack -s "sub: attachment" attachment_file johndoe@somedomain.com