Configure mailx to Relay via a Google SMTP Server

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mailx 12.5 7/5/10

Overview

This article describes how to configure mailx to send command-line e-mail by relay-ing it via the Google SMTP server.

Create a Dedicated User

This step is optional, but it is a good idea to use a separate "service" account to send service e-mails. The remaining of the example assumes a "service@novaordis.com" was created and it is operational.


Important If the service account was specifically created for this job, you will need to log in at least one time via the web interface (to accept terms and conditions and possibly to change the password), otherwise sending e-mails will fail with "Please log in via your web browser and then try again."

Configure GMail

It is possible to send the e-mail via Google SMTP servers using two mechanisms: GMail SMTP relay service and configuring "Google Apps SMTP settings to send mail from a printer, scanner, or app". This document describes the former. Details on how to use "Google Apps SMTP settings to send mail from a printer, scanner, or app" are available here: https://support.google.com/a/answer/176600?hl=en

Configuring GMail SMTP Relay Service

This procedure describes how to configure Google Apps GMail to accept relaying from a specific IP address or set of addresses. Note that is optional, we can solely rely on login authentication, but it is safer.


Google Apps Admin Console -> Apps -> Google Apps -> GMail -> Advanced settings -> "General Settings" tab -> SMTP relay service -> Edit:

GMailSMTPRelayService.png

Turn on all protection mechanisms available:

  • source IP address
  • SMTP authentication
  • TLS encryption

mailx Configuration

Insure Access to a Valid NSS Certificate Database

You will need to make sure mailx has access to a valid Google certificate in an NSS certificate database. Firefox usually has it in its profile directory, but it is a good idea to initialize a private certificate database. The following page explain how to do that:

Create a New NSS Certificate Database and Import Google's Certificate

This page explains how to "re-use" Firefox Mozilla certificate database:

Re-Use the Firefox NSS Certificate Database

Assuming you provision root GMail SMTP access, move the certs directory created at the previous step under ~root/etc/certs as follows:

mv .../certs ~root/etc/certs

mail.rc Configuration

Configure /etc/mail.rc as follows:

...

account gmail {

set smtp-auth=login
set smtp=smtps://smtp-relay.gmail.com
set from="service@example.com"
set smtp-auth-user=service@novaordis.com
set smtp-auth-password="PASSWORD"
set ssl-verify=ignore
set nss-config-dir=/root/etc/certs
}

Important

  • the "s" in "smtps://" is important.
  • the @example.com in the "set from=service@example.com" is important, this is what GMail uses to look up the domain's SMTP relay settings. It also uses "ehlo".

What to Avoid

Do NOT set smtp-use-starttls. If you do that, you'll get:

...
>>> STARTTLS
503 5.5.1 bad sequence of commands ck3sm4808076igb.6 - gsmtp
smtp-server: 503 5.5.1 bad sequence of commands ck3sm4808076igb.6 - gsmtp

Do NOT use set smtp=smtps://smtp-relay.gmail.com:587, otherwise you'll get:

Resolving host smtp-relay.gmail.com . . . done.
Connecting to 173.194.202.28:587 . . . connected.
SSL/TLS handshake failed: Unknown error -5938.

mail.rc Permissions

mail.rc contains password, so restrict its permissions:

chmod go-rwx /etc/mail.rc

Test

echo "test" | mailx -v -A gmail -s "test" test@example.com

Still Quite Not All Right

I am getting a certificate error even after using Mozilla's certificates. The e-mail goes through, tough:

[root@now510]# echo "test" | mailx -v -A gmail -s "test" test@example.com
Resolving host smtp-relay.gmail.com . . . done.
Connecting to 173.194.203.28:smtps . . . connected.
Error in certificate: Peer's certificate issuer is not recognized.
Comparing DNS name: "smtp-relay.gmail.com"
SSL parameters: cipher=AES-128-GCM, keysize=128, secretkeysize=128,
issuer=CN=Google Internet Authority G2,O=Google Inc,C=US
subject=CN=smtp-relay.gmail.com,O=Google Inc,L=Mountain View,ST=California,C=US
220 smtp-relay.gmail.com ESMTP r8sm1213882igg.3 - gsmtp
>>> EHLO now510
250-smtp-relay.gmail.com at your service, [104.50.201.83]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-CHUNKING
250 SMTPUTF8
>>> AUTH LOGIN
334 ...
>>> ...
334 ...
>>> ...
235 2.7.0 Accepted
>>> MAIL FROM:<service@....com>
250 2.1.0 OK r8sm1213882igg.3 - gsmtp
>>> RCPT TO:<test@example.com>
250 2.1.5 OK r8sm1213882igg.3 - gsmtp
>>> DATA
354  Go ahead r8sm1213882igg.3 - gsmtp
>>> .
250 2.0.0 OK 1458199638 r8sm1213882igg.3 - gsmtp
>>> QUIT
221 2.0.0 closing connection r8sm1213882igg.3 - gsmtp