Configure Sendmail to Use Gmail Relay on Ubuntu 18.04/Debian 10/9

In this guide, we are going to learn how to configure Sendmail to use Gmail Relay on Ubuntu 18.04/Debian 10/9. Sendmail can be configured to relay mails via external mail servers including Gmail SMTP.

Configure Sendmail to Use Gmail Relay on Ubuntu 18.04/Debian 10/9

Install Sendmail on Ubuntu 18.04/Debian 10/9

Before you can install Sendmail, ensure that you remove other existing MTAs such as Postfix.

apt --purge autoremove postfix

Next, install Sendmail and other mail utilities if not installed already.

apt install sendmail sendmail-bin mailutils

Define Gmail Authentication Details

Next, you need to create a directory to store a file that defines how to connect to Gmail SMTP server for mail relay. Hence, create a directory as shown below;

mkdir -m 700 /etc/mail/authinfo

Next, create a file to store Gmail authentication details under the directory created above.

vim /etc/mail/authinfo/gmail-smtp-auth

The file should define Gmail authentication information should contain the line below;

AuthInfo: "U:root" "I:[email protected]" "P:GMAIL_USER_PASSWORD"

Where:

• U (The user (authorization) identifier): defines the name of the user that sendmail will use to check allowable permissions.
• I (The authentication Identifier): Name of the user allowed to setup a connection.
• P: The clear text for the authentication user used to authorize the mail connections.

Replace USER ID and GMAIL_USER_PASSWORD with your Gmail account user ID and password respectively.

Create Sendmail-Gmail Authentication Database Map

Next, you need to generate the Sendmail gmail authentication databas map from the above authentication information. You can use the makemap utility as shown below;

makemap hash /etc/mail/authinfo/gmail-smtp-auth < /etc/mail/authinfo/gmail-smtp-auth

This will create authentication database, /etc/mail/authinfo/gmail-smtp-auth.db.

Configure Sendmail Smart Host

A smart host/smarthost is used to specify an SMTP server that relays emails, in this case, smtp.gmail.com. This can be defined using SMART_HOST macro.

The definition should made in /etc/mail/sendmail.mc configuration file JUST BEFORE the MAILER definition. If you need to create a comment, begin a line with dnl.

Note the line;

FEATURE(authinfo',hash -o /etc/mail/authinfo/gmail-smtp-auth.db')dnl

Replace it with your Gmail Authentication sendmail database map you generated above.

vim /etc/mail/sendmail.mc

...
dnl #
dnl # Defining Gmail Smarthost for sendmail
define(`SMART_HOST',`[smtp.gmail.com]')dnl
define(`RELAY_MAILER_ARGS', `TCP $h 587')dnl
define(`ESMTP_MAILER_ARGS', `TCP $h 587')dnl
define(`confAUTH_OPTIONS', `A p')dnl
TRUST_AUTH_MECH(`EXTERNAL DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
define(`confAUTH_MECHANISMS', `EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
FEATURE(`authinfo',`hash -o /etc/mail/authinfo/gmail-smtp-auth.db')dnl
dnl #
dnl # Default Mailer setup
MAILER_DEFINITIONS
MAILER(`local')dnl
MAILER(`smtp')dnl

Regenerate Sendmail Configuration

Save the configuration file above and re-build Sendmail configuration.

make -C /etc/mail

...
Creating /etc/mail/relay-domains
# Optional file...
Updating Makefile ...
Reading configuration from /etc/mail/sendmail.conf.
Validating configuration.
Creating /etc/mail/Makefile...
Updating sendmail.cf ...
The following file(s) have changed:
  /etc/mail/relay-domains /etc/mail/sendmail.cf
** ** You should issue `/etc/init.d/sendmail reload` ** **
make: Leaving directory '/etc/mail'

Reload Sendmail

After rebuilding Sendmail configuration, reload Sendmail.

/etc/init.d/sendmail reload

Testing Sendmail Gmail Relay

To verify that the setup actually works, try to send a test mail using sendmail. For example;

echo "This is a test for sendmail gmail relay" | sendmail [email protected]

You should be able to receive a mail with a body, This is a test for sendmail gmail relay. Also check the mail logs.

That is all on how to configure Sendmail to use Gmail relay on Ubuntu 18.04/Debian 10/9.

Install Zimbra Mail Server on Fedora 30/29/CentOS 7

Encrypt Emails using Enigmail on Thunderbird

Configure Postfix to Use Gmail SMTP on Ubuntu 18.04

How to Install and Setup Roundcube Webmail on Debian 9

How to Install and Setup iRedMail Mail Server on Ubuntu 18.04 LTS

How to Install and Setup Thunderbird Mail Client on Ubuntu 18.04