Hi,

Thanks for the tutorial, it's very clear and easy to follow. I have a problem though, and I've exhausted every method I can think of to solve it. 

When using the sample PHP script above to send the message (through gmail), I get the following error:

errormsg='authentication failed (method PLAIN)' exitcode=EX_NOPERM

I have followed the config settings to the letter, checked the php.ini path, etc. but to no avail. Any suggestions on where to start looking to solve this?



By the way, I can tell than an attempt to send the message through gmail was made because I received a message from Google about an unauthorized attempt to send email through my account. I double checked the password, file settings, file location, but all seems correct.

@wizardware: Google prevented the login so php was unable to send the message. Try to see if you can whitelist your app from your gmail account's settings.

Bingo!
That did the trick, problem solved. Thank you Kamal, I doubt I would have ever thought of this.


It looks like msmtp expects to see the system wide config file in /etc/msmtprc in spite of what you put in the sendmail path. You also need to change the SMTP port to 587 to work with gmail - at least for my paid Google Apps account.

Ignore my comment - i'd missed out the chown. After some sleuthing, I found the reason!

CentOS 6.4 x32 does not send e-mail in error: "msmtp: support for TLS is not compilled in".
How to fix the problem?

This method is not safe to use on shared environments, since the gmail/yahoo password is exposed and readable by any apache user.

@dmmd Add "tls_certcheck off" to the msmtp configuration file.

Hi there, great guide!  It's helped a lot, but I seem to be having issues getting the actual PHP to work.

Using command line msmtp command seems to work correctly, however using the PHP file sends back the failiure message.  Just running "php mail.php" sends a "Authentication Failed (xxx Too Many Login Attempts)" which really confuses me.  How could the command line email pass authentication but not the php file?

Thanks!

<h3>What the Red Means</h3>

The lines that the user needs to enter or customize will be in red in this tutorial!
 
The rest should mostly be copy-and-pastable.

<h3>About PHP mail()</h3>

The PHP <a href="http://php.net/manual/en/function.mail.php" target="_blank">mail()</a> function uses the program in <a href="http://www.php.net/manual/en/mail.configuration.php#ini.sendmail-path" target="_blank">sendmail_path</a> configuration directive to send emails. This is set up as sendmail by default.

While most Linux installations have sendmail preinstalled, there is always a hassle of setting up SPF/PTR records, generating DKIM keys and a lot more to ensure that the email sent by your PHP script is not flagged as spam. A SMTP client called MSMTP can be used to send emails using third-party SMTP servers, this can also be used by PHP&#39;s mail() in the place of sendmail.

<h2>Installation</h2>

To install MSMTP on Fedora Linux use yum:

<pre>yum install msmtp</pre>

CentOS repository doesn&#39;t have a RPM package for MSMTP so we need to install it from source:

<pre>yum install make gcc pkgconfig
wget <a href="http://sourceforge.net/projects/msmtp/files/msmtp/1.4.31/msmtp-1.4.31.tar.bz2/download" target="_blank">http://sourceforge.net/projects/msmtp/files/msmtp/1.4.31/msmtp-1.4.31.tar.bz2/download</a>
tar -xvf msmtp-1.4.31.tar.bz2
cd msmtp-1.4.31
./configure
make
make install</pre>

The latest version is 1.4.31 at the time of this writing but it may change in future so to get the latest version, visit <a href="http://sourceforge.net/projects/msmtp/files/msmtp/" target="_blank">this sourceforge page</a>.

On Ubuntu/Debian distribution use apt-get:

<pre>apt-get install msmtp</pre>

Arch Linux users:

<pre>sudo pacman -S msmtp</pre>

<h2>Configuring MSMTP</h2>

The configuration file of MSMTP is stored in ~/.msmtprc for each user and /etc/msmtprc is the 
system wide configuration file.
Open the configuration file in your directory.


<pre>vi ~/.msmtprc</pre>

Add the following lines for a Yahoo account:

<pre>account yahoo
tls on
tls_starttls off
tls_certcheck off
auth on
host <a href="http://smtp.mail.yahoo.com" target="_blank">smtp.mail.yahoo.com</a>
user user1
from user1@yahoo.com
password yourYahooPa5sw0rd</pre>

For Gmail, use the following settings:

<pre>account gmail
tls on
tls_certcheck off
auth on
host <a href="http://smtp.gmail.com" target="_blank">smtp.gmail.com</a>
port 587
user user1@gmail.com
from user1@gmail.com
password yourgmailPassw0rd</pre>
This file can also have more than one account, just ensure that the &quot;account&quot; value is unique for each section.
Save the file and use chmod to make this file readable only by the owner since it contains passwords.
This step is mandatory because msmtp won&#39;t run if the permissions are more than 600.
<pre>chmod 600 ~/.msmtprc</pre>

Before implementing this in PHP, check from the command-line to ensure it works properly. To do this, create a plain text file containing a simple email:

<pre>echo -e &quot;From: alice@example.com \n\
To: bob@domain.com \n\
Subject: Hello World \n\
\n\
This email was sent using MSMTP via Gmail/Yahoo.&quot; &gt;&gt; sample_email.txt</pre>

Now send this email:

<pre>cat sample_email.txt | msmtp --debug -a gmail bob@domain.com</pre>

Replace the word &quot;gmail&quot; with &quot;yahoo&quot; or whatever you entered for the &quot;account&quot; option. You&#39;ll see a lot of messages because of the
&quot;--debug&quot; parameter. This is to make troubleshooting easy if things don&#39;t work as expected.
If bob@domain.com receives this email, everything is setup correctly so copy this file to the /etc directory:

<pre>cp -p ~/.msmtprc /etc/.msmtp_php</pre>

Change the ownership to the username under which the web server is running. This can be &quot;apache&quot;, &quot;www-data&quot;, or &quot;nobody&quot; depending on the Linux distribution on your VPS and web server installed:

<pre>chown www-data:www-data /etc/.msmtp_php</pre>

<h2>Configuring PHP</h2>

Open the php.ini file, its location varies according to the OS and PHP type installed (PHP CGI, mod_php, PHP-FPM etc):

<pre>vi /etc/php5/php.ini</pre>

Find the following line:

<pre>sendmail_path =</pre>

Modify it by adding the path to the msmtp command:

<pre>sendmail_path = &quot;/usr/bin/msmtp -C /etc/.msmtp_php --logfile /var/log/msmtp.log -a gmail -t&quot;</pre>

Manually create a log file and change its ownership to the username your web server is running as:

<pre>touch /var/log/msmtp.log
chown www-data:www-data /var/log/msmtp.log</pre>

Restart your web server to apply the changes:

<pre>service httpd restart</pre>

In Arch Linux, this is done using the systemctl command:

<pre>systemctl restart httpd</pre>

Depending on your OS and web server, replace &quot;httpd&quot; with the appropriate name. If PHP is running as a separate process (like PHP-FPM), restart it instead:

<pre>service php5-fpm restart</pre>

Create a PHP script with a simple mail() to test this setup:

<pre>&lt;?php
if(mail(&quot;receipient@domain.com&quot;,&quot;A Subject Here&quot;,&quot;Hi there,\nThis email was sent using PHP&#39;s mail function.&quot;))
print &quot;Email successfully sent&quot;;
else
print &quot;An error occured&quot;;
?&gt;</pre>

Access this file from the web browser.

<pre>http://<a href="http://www.example.com" target="_blank">www.example.com</a>/file.php</pre>

If this email wasn&#39;t sent you can check the msmtp log file for errors.

<pre>tail /var/log/msmtp.log</pre>

<h2>Common errors</h2>

If the email was not sent when using the PHP script, troubleshoot as follows:

<ul>
<li>Check if you edited the correct php.ini file. This can be confirmed by creating a phpinfo(); file and checking the &quot;Loaded Configuration File&quot; section.</li>
<li>The path to the msmtp configuration file might be wrong or the web server doesn&#39;t have permission to read this file.</li>
<li>Check if an email is sent by running the script using command-line PHP:
<pre>php /var/www/html/file.php</pre></li></ul>

Read through this tutorial to learn how to use Gmail or Yahoo with PHP mail() function.