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I have a new Ubuntu 18.04 system and want to have mdadm, smartd, et al. to send warning emails through my gmail account. I have followed the guides in How can I configure Postfix to send all email through my Gmail account? and How to configure Postfix to use Gmail SMTP on Ubuntu 16.04 / 17.10, but I keep getting authentication failures. I have two-factor authentication (2FA) set up with my gmail account. Could this be a factor?

  • Yes that the issue please check google as they should an option to use special app credentials where 2FA is impossible – George Udosen Aug 21 '18 at 10:30
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Please follow this guide to get it working as 2FA affects these apps but here is a summary:

  1. Visit your App passwords page. You may be asked to sign in to your Google Account.
  2. At the bottom, click Select app and choose the app you’re using.
  3. Click Select device and choose the device you’re using.
  4. Select Generate.
  5. Follow the instructions to enter the App password (the 16 character code in the yellow bar) on your device.
  6. Select Done.

Once you are finished, you won’t see that App password code again. However, you will see a list of apps and devices you’ve created App passwords for.

READ MORE:

https://duo.com/blog/bypassing-googles-two-factor-authentication

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As George suggested, 2FA was indeed a factor. I wrote down the full procedure below that solved my problems:

Install packages

sudo apt-get install postfix mailutils libsasl2-2 ca-certificates libsasl2-modules
  • Select Internet host.
  • Enter a hostname (does not have to be known to the internet), e.g., trillian.at.home.

Get app password from google

Google allows you to set up 'apps' that have their own password. This technique works with mail relays, too.

  • Visit your app passwords page (https://security.google.com/settings/security/apppasswords).
  • Log in using your two-factor authentication method.
  • Select app: Mail and device: Other.
  • Give your 'app' a name, e.g., mail relay from <hostname>.
  • Press Generate.
  • Write down the 'app' password (16 characters, no spaces).

Store the app password

Open/create a password file:

sudo nano /etc/postfix/sasl/relay_passwd

Put the following text in the file:

[smtp.gmail.com]:587 USERNAME@gmail.com:APP-PASSWORD

where USERNAME is your gmail username and APP-PASSWORD is the 16-digit app password.

Create a hash file:

sudo postmap /etc/postfix/sasl/relay_passwd

Ensure that only root can read/write the password files:

sudo chown root:root /etc/postfix/sasl/relay_passwd /etc/postfix/sasl/relay_passwd.db
sudo chmod 0600 /etc/postfix/sasl/relay_passwd /etc/postfix/sasl/relay_passwd.db

Create a certificate file

cat /etc/ssl/certs/thawte_Primary_Root_CA.pem | sudo tee -a /etc/postfix/cacert.pem

Configure postfix

sudo nano /etc/postfix/main.cf

Remove the relayhost line and ensure that the following lines are in the file.

relayhost = [smtp.gmail.com]:587
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/sasl/relay_passwd
smtp_sasl_security_options = noanonymous
smtp_tls_CAfile = /etc/postfix/cacert.pem
smtp_use_tls = yes

Test

Run

echo "Test email" | mail -s "Test" you@gmail.com

Hopefully your mail has appeared at gmail. Otherwise, use mailq and tail -f /var/log/mail.log for debugging.

Set up mdadm and smartd

If the test email arrived, you can now set up mdadm and smartd. For mdadm, I use the line

MAILADDR MY-GMAIL-USERNAME+mdadm-trillian@gmail.com

in /etc/mdadm/mdadm.conf to enable mail filtering in my gmail inbox. Similarly, I use the text

-m MY-GMAIL-USERNAME+smartd-trillian@gmail.com

in my DEVICESCAN line in /etc/smartd.conf.

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