Send authenticated gmail from command line


You can send basic email from the command line. That’s been done a million times before, including by me!
Did you know that you can send email from the command line, from your gmail account that you authenticated to? That’s a big deal for some people. This document describes how to do that.

Sending gmail from command line

Install packages msmtp and mutt.
yum install msmtp mutt
Write the conf file and fill in the pertinent information.
# write conf file
touch "${tf}"; chmod 0600 "${tf}"; chown root:root "${tf}";
cat <<EOF >"${tf}"
account default
tls on
tls_certcheck off
auth on
port 587
password plaintextpassword
account second
tls on
tls_certcheck off
auth on
port 587
password plaintextpassword

Now you can send an email with this command.
echo -e "From: Pretty Name\r\nSubject: Example subject\r\nContent goes here." | msmtp --debug --from=default -t

Sending attachments

Configure mutt if you want to send attachments from the command line.
cat <<EOF >> /etc/Muttrc.local
set sendmail="/usr/bin/msmtp"
set use_from=yes
set realname="Pretty Name"
set envelope_from=yes

Send an email in html format and with an attachment.
subject="This is the subject
Mime-Version: 1.0
Content-Type: text/html"
mutt -a ~/attachment.txt -s "${subject}" -- << EOF
This will be fixed width font. I find it useful for sending code fragments or log files.

Authenticating to gmail from command line

The Arch Linux wiki provides an important reminder:

Tip: If using Gmail you’ll need to either

  • Allow “Less Secure Apps” in Settings > Security. Make sure to sign out of your other Gmail accounts first because the security settings part of Google Accounts can not manage concurrent sessions of more than one account.
  • Enable two factor authentication and create an app password.


  1. from bgscripts package

Adding ADFS integration to Apache


ADFS is Microsoft Active Directory Federated Services. It is a single sign-on solution, and this post explains how to tie in Apache 2.4 (CentOS 7) to ADFS. All of this works even with SELinux enforcing!

The test environment described by this document includes the following.

Root URL: (

Protected subdirectory:

Warning! ADFS Configuration changes can take a few minutes to take effect.

Adding ADFS integration to Apache

This guide assumes you have a functional apache environment.

Configuring apache

Install mod_auth_mellon from the regular centos repository. Also include php.

yum -y install mod_auth_mellon php

Set up mellon with the sample hostname and url using the provided tool.

mkdir -p /etc/httpd/mellon
cd /etc/httpd/mellon
/usr/libexec/mod_auth_mellon/ ""

This script outputs 3 files to the current directory.

This certificate is a self-signed certificate, but other options can be used and should be considered for production environments. Be aware that the certificates are also dumped into the xml file that will be shared with the ADFS host, so be sure to share any new certificates there as well.

Collect the ADFS metadata and store it locally. Such metadata is usually available at a URL similar to the following.

Here is a copy-pastable line for people like me.

wget -O /etc/httpd/mellon/FederationMetadata.xml

Build the apache Mellon config.

cat <<EOF >/etc/httpd/conf.d/auth_mellon.conf
MellonCacheSize 100
MellonLockFile /var/run/mod_auth_mellon.lock
MellonPostTTL 900
MellonPostSize 1073741824
MellonPostCount 100
MellonPostDirectory "/var/cache/mod_auth_mellon_postdata"

My test environment uses a modular ssl directives include file:

cat <<EOFSSL >/etc/httpd/sites/all-ssl.cnf
SSLEngine on
SSLProtocol all -SSLv2 -SSLv3
SSLHonorCipherOrder on

<Files ~ "\.(cgi|shtml|phtml|php3?)$">
        SSLOptions +StdEnvVars
<Directory "/var/www/cgi-bin">
        SSLOptions +StdEnvVars

SSLCertificateFile /etc/pki/tls/certs/localhost.crt
SSLCertificateKeyFile /etc/pki/tls/private/localhost.key

SetEnvIf User-Agent ".*MSIE 4\.0b2.*"                 nokeepalive ssl-unclean-shutdown                 downgrade-1.0 force-response-1.0

LogLevel warn
ErrorLog logs/ssl_error_log
CustomLog logs/ssl_access_log combinedvhost

<Directory "/var/www/html/notfound/">
        AllowOverride None
        Order allow,deny
        Allow from all

# END OF FILE all-ssl.cnf

In the apache config, probably /etc/httpd/sites/sample.conf, modify the virtual host.

cat <<EOF >/etc/httpd/sites/sample.conf


        ServerAlias     sample

        # Redirect everything to the https site
        RewriteEngine   On
        RewriteRule ^(.*)$      https://%{HTTP_HOST}%{REQUEST_URI}



        ServerAlias     sample
        DocumentRoot /var/www/html/

        Include sites/all-ssl.cnf

        <Directory "/var/www/html/">
            AllowOverride None
            Order allow,deny
            Allow from all
            Options Indexes FollowSymLinks

        <Location /auth1/>
                # Mellon auth which goes to ADFS
                Include sites/adfs.cnf
                MellonCond "groups" "WebAppUsers_grp" [REG,SUB,NC]

Make the post dump location, which is not necessary but might be useful in the future.

mkdir -p /var/cache/mod_auth_mellon_postdata
chown apache:apache /var/cache/mod_auth_mellon_postdata
chmod 0700 /var/cache/mod_auth_mellon_postdata

Building the include files

We already built the all-ssl.cnf include file, so we just need the adfs include file.

cat <<EOF >/etc/httpd/sites/adfs.cnf
# File: /etc/httpd/sites/adfs.cnf
MellonEnable "auth"
Require valid-user
AuthType "Mellon"
MellonVariable "cookie"
#MellonSamlResponseDump On

MellonSPPrivateKeyFile /etc/httpd/mellon/
MellonSPCertFile /etc/httpd/mellon/
MellonSPMetadataFile /etc/httpd/mellon/
MellonIdPMetadataFile /etc/httpd/mellon/FederationMetadata.xml
MellonMergeEnvVars On ":"
MellonEndpointPath /auth1/endpoint

Here, the MellonMergeEnvVars On “:” means that any multiple-value attribute (like Groups) will be added to one colon-delimited string instead of being assigned to “Mellon_Groups_1” “Mellon_Groups_2” and so on. It’s how the MellonCond works in the virtual host configuration.

Building example sites

Build the index file for the protected directory.

cat <<EOF >/var/www/html/
<head><title>Authorized zone</title></head>
<h1>Welcome to the authorized zone.</h1>
You should only be able to see this if you are authenticated and authorized.

Make a php troubleshooting file.

cat <<EOF >${thisfile}
chown apache:apache ${thisfile}
chmod 644 ${thisfile}

This little php file will show the apache environment variables that are available for use in the apache directives. The important ones here will be the ones prepended with “MELLON_.”

Configuring ADFS to share data

On the ADFS server, add a new relying party trust.

Run the AD FS management tool.

Navigate in the tree structure to AD FS –> Trust relationships –> Relying party trusts.

Select on the action menu “Add relying party trust…”

The easiest way to do this is to use the xml file generated by that script earlier.

Do not configure multi-factor authentication.

Permit all users to access this relying party.

Edit the properties of the relying party trust –> Advanced tab.

Set value “Secure hash algorithm” to SHA-1.

Adding claim rules

Right-click this relying party trust and select “Edit Claim Rules.”

Add a rule of type “Transform incoming claim.”

Incoming claim type: Windows account name
Outgoing claim type: Name ID
Outgoing name ID format: Transient Identifier
Radio button: Pass through all claim values

The rule text looks like:

c:[Type == ""]
 => issue(Type = "", Issuer = c.Issuer, OriginalIssuer = c.OriginalIssuer, Value = c.Value, ValueType = c.ValueType, Properties[""] = "urn:oasis:names:tc:SAML:2.0:nameid-format:transient");

Reference: Specific example of mellon configuration

Add custom rule “Get all groups user belongs to.”

c:[Type == "", Issuer == "AD AUTHORITY"]
 => add(store = "Active Directory", types = (""), query = ";tokenGroups;{0}", param = c.Value);

The add command instead of issue passes the information on to the next rule.

Reference: Custom rules sharing

Add custom rule “Filter your groups only.”

c:[Type == "", Value =~ ".*WebAppUsers_grp.*|.*IT.*"]
 => issue(Type = "groups", Value = c.Value, Issuer = c.Issuer);

The type name of “groups” means that mellon will provide an apache environment variable of “MELLON_groups” which we are performing the condition statement on in the virtual host.

The regex in the first part is looking for any group name that has “IT” in it at all or “WebAppUsers_grp” which is probably pretty specific to just that one group.

What this does is limit the groups being sent so instead of those 538 AD groups possible that that one user is in, it will pass back only the 28 IT department-related ones and the WebAppUsers_grp.

After the apachectl configtest, give apache graceful a shot!

The above link (modified for you of course) should redirect to the AD FS login page and then send authenticated users back!

The benefits here include using apache as a reverse proxy to tomcat applications (local or otherwise) and providing a layer of authentication.


  1. Official mellon page
  2. Specific example of mellon configuration
  4. ADFS saml rules
  5. Regex is allowed in claims
  7. Custom rules sharing