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2014-10-14-how-to-relay-postfix-mails-via-smtp.gmail.com-on-ubuntu-14.04.markdown

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How To Relay Postfix mails via smtp.gmail.com on Ubuntu 14.04.1
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neoark

Introduction:

This guide will help you to use a Gmail account as a free SMTP server on your Ubuntu-Linux server 14.04. Once configured, all emails from your server will be sent via Gmail. This method will be useful if you have many sites on your server and want them all to send emails via Gmail’s SMTP server. Please Limits Google's Sending to see the amount of mail one user can send. Steps:

Install all necessary packages:

$ sudo apt-get install postfix mailutils libsasl2-2 ca-certificates libsasl2-modules nano

Postfix configuration wizard will ask you some questions. Just select your server as Internet Site and for FQDN use something like mail.your_domain.com

Then open your postfix config file:

$ nano /etc/postfix/main.cf

add/modify the following lines:

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

Validate Certificate & Open/Create sasl_passwd:

$ cat /etc/ssl/certs/Thawte_Premium_Server_CA.pem | sudo tee -a /etc/postfix/cacert.pem 
$ sudo nano /etc/postfix/sasl/sasl_passwd

And add following line:

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

If you want to use your Google App’s domain, replace @gmail.com with your @domain.com. Also for PASSWORD use Google App password if you have enabled 2-Step-Verification.

Set sasl_passwd file permission and update postfix config to use sasl_passwd file:

$ sudo chmod 400 /etc/postfix/sasl/sasl_passwd
$ sudo postmap /etc/postfix/sasl/sasl_passwd

Reload postfix config for changes to take effect:

$ sudo /usr/sbin/postfix reload

Testing:

If you have configured everything correctly, following command should generate a test mail from your server to your mailbox. Replace you@example.com with your email address.

$ echo "Test mail from postfix" | mail -s "Test Postfix" you@example.com

Other Notes:

This will work with any mail server that provides SMTP relaying.

Troubleshooting:

  • Monitor postfix mail log in a separate session with the following command:

        $ tail -f /var/log/maillog

  • If you receive the following error in your maillog file:

      postfix/smtp[3191]: AAC325FA46: SASL authentication failed; server smtp.gmail.com[64.233.166.108] said: 534-5.7.14 <https://accounts.google.com/ContinueSignIn?someverylongurl> Please log in via your web browser and then try again.?534-5.7.14 Learn more at?534 5.7.14 https://support.google.com/mail/bin/answer.py?answer=78754 c214wjb.23 - gsmtp

Follow steps on Allowing less secure apps to access your account. If the error still persist turn on Google's [2-Step-Verification] (https://support.google.com/accounts/answer/185839?hl=en&ref_topic=1099588) and Sign in using App Passwords to resolve the error.