Tutorial

How To Use Gmail or Yahoo with PHP mail() Function

Published on August 3, 2013

Jesin A

How To Use Gmail or Yahoo with PHP mail() Function

What the Red Means

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.

About PHP mail()

The PHP mail() function uses the program in sendmail_path 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's mail() in the place of sendmail.

Installation

To install MSMTP on Fedora Linux use yum:

yum install msmtp

CentOS repository doesn't have a RPM package for MSMTP so we need to install it from source:

yum install make gcc pkgconfig
wget http://sourceforge.net/projects/msmtp/files/msmtp/1.4.31/msmtp-1.4.31.tar.bz2/download
tar -xvf msmtp-1.4.31.tar.bz2
cd msmtp-1.4.31
./configure
make
make install

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 this sourceforge page.

On Ubuntu/Debian distribution use apt-get:

apt-get install msmtp

Arch Linux users:

sudo pacman -S msmtp

Configuring MSMTP

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.

vi ~/.msmtprc

Add the following lines for a Yahoo account:

account yahoo
tls on
tls_starttls off
tls_certcheck off
auth on
host smtp.mail.yahoo.com
user user1
from user1@yahoo.com
password yourYahooPa5sw0rd

For Gmail, use the following settings:

account gmail
tls on
tls_certcheck off
auth on
host smtp.gmail.com
port 587
user user1@gmail.com
from user1@gmail.com
password yourgmailPassw0rd

This file can also have more than one account, just ensure that the "account" 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't run if the permissions are more than 600.

chmod 600 ~/.msmtprc

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:

echo -e "From: alice@example.com \n\
To: bob@domain.com \n\
Subject: Hello World \n\
\n\
This email was sent using MSMTP via Gmail/Yahoo." >> sample_email.txt

Now send this email:

cat sample_email.txt | msmtp --debug -a gmail bob@domain.com

Replace the word "gmail" with "yahoo" or whatever you entered for the "account" option. You'll see a lot of messages because of the "--debug" parameter. This is to make troubleshooting easy if things don't work as expected. If bob@domain.com receives this email, everything is setup correctly so copy this file to the /etc directory:

cp -p ~/.msmtprc /etc/.msmtp_php

Change the ownership to the username under which the web server is running. This can be "apache", "www-data", or "nobody" depending on the Linux distribution on your VPS and web server installed:

chown www-data:www-data /etc/.msmtp_php

Configuring PHP

Open the php.ini file, its location varies according to the OS and PHP type installed (PHP CGI, mod_php, PHP-FPM etc):

vi /etc/php5/php.ini

Find the following line:

sendmail_path =

Modify it by adding the path to the msmtp command:

sendmail_path = "/usr/bin/msmtp -C /etc/.msmtp_php --logfile /var/log/msmtp.log -a gmail -t"

Manually create a log file and change its ownership to the username your web server is running as:

touch /var/log/msmtp.log
chown www-data:www-data /var/log/msmtp.log

Restart your web server to apply the changes:

service httpd restart

In Arch Linux, this is done using the systemctl command:

systemctl restart httpd

Depending on your OS and web server, replace "httpd" with the appropriate name. If PHP is running as a separate process (like PHP-FPM), restart it instead:

service php5-fpm restart

Create a PHP script with a simple mail() to test this setup:

<?php
if(mail("receipient@domain.com","A Subject Here","Hi there,\nThis email was sent using PHP's mail function."))
print "Email successfully sent";
else
print "An error occured";
?>

Access this file from the web browser.

http://www.example.com/file.php

If this email wasn't sent you can check the msmtp log file for errors.

tail /var/log/msmtp.log

Common errors

If the email was not sent when using the PHP script, troubleshoot as follows:

Check if you edited the correct php.ini file. This can be confirmed by creating a phpinfo(); file and checking the "Loaded Configuration File" section.
The path to the msmtp configuration file might be wrong or the web server doesn't have permission to read this file.
Check if an email is sent by running the script using command-line PHP:
```
php /var/www/html/file.php
```

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About the author(s)

Jesin A

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wizardware • September 14, 2013

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?

wizardware • September 14, 2013

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.

Kamal Nasser

DigitalOcean Employee

• September 15, 2013

@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.

wizardware • September 15, 2013

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

Ian Waring • November 5, 2013

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.

Ian Waring • November 5, 2013

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

dmmd • November 6, 2013

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

karitelis • May 30, 2015

I had the same problem on CentOS 7 with msmtp version 1.6.2 this is how I solved it: In the directory where the source code of msmtp is located run these commands

make uninstall make clean yum install -y openssl* ./configure --with-tls=openssl make make install

That’s all =)

zeokat • November 10, 2013

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

Jesin A • November 27, 2013

@dmmd Add “tls_certcheck off” to the msmtp configuration file.

emapparition • December 3, 2013

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!

Jesin A • December 4, 2013

@em.apparition That error is displayed by the SMTP server (usually Gmail’s SMTP) if you’re using Google Apps without a DKIM record.

Read this http://serverfault.com/questions/543007/google-smtp-error-454-4-7-0-too-many-login-attempts-please-try-again-later

As to why it succeeds with the msmtp command I’m guessing that you’re using different email accounts in the ~/.msmtprc file and the one in /etc

nh3092 • January 1, 2014

something missing that make me crazy

yum install openssl yum install openssl-devel

and check send mail path

msmtp --version

jntslvdrt • January 25, 2014

I couldn’t send it from file.php but it worked on php /var/www/html/file.php What did I do wrong?

jhaankitesh • May 10, 2016

did you solve it?

jntslvdrt • January 26, 2014

I made it work. But not on 465 port. Actually I’m on 587… but would be more secure to use 465? I tried to exchange from 587 to 465 but with no success. I tried add ssl:// on smtp.gmail.com and no email wass ent

luanpersini • January 27, 2014

I cant get it working… Tryed postfix, sendmail, exim and now this, none work. Unnistalled everything before testing and followed the many tutorials. Using unbutu 12.4

On this one im having problem on step cat sample_email.txt | msmtp --debug -a gmail bob@domain.com

msmtp: cannot connect to smtp.gmail.com, port 587: Network is unreachable msmtp: could not send mail (account gmail from /home/username/.msmtprc)

lfna23 • January 29, 2014

This is the first time I’m doing stuff like this, so I almost don’t have any idea. My msmtprc file looks like this:

account killaribyte host mail.killaribyte.com port 587 from contacto@killaribyte.com user contacto password **********

When I run the command: dig MX killaribyte.com +short @ns1.digitalocean.com I got: 50 mail.killaribyte.com.

When I run: host mail.killaribyte.com ns1.digitalocean.com I got: Using domain server: Name: ns1.digitalocean.com Address: 198.199.120.125#53 Aliases:

mail.killaribyte.com has address ... (my IP)

And finally when I want to test it with: cat sample_email.txt | msmtp --debug -a killaribyte contacto@killaribyte.com I got: msmtp: cannot connect to mail.killaribyte.com, port 587: Connection refused msmtp: could not send mail (account killaribyte from /etc/msmtprc)

Jesin A • January 31, 2014

@lfna23 Try changing the port to 25

@luanpersini I think iptables is configured incorrectly to block outgoing connections or to prevent TCP connections. Try clearing the rules

<pre>iptables -X iptables -F</pre>

spenny • April 21, 2014

The command line of sending e mail works for me but when it comes to using the file.php, I encountered the error msg in the browser "Failed to connect to ssl://foeapp.com:465 [SMTP: Failed to connect socket: Connection refused (code: -1, response: )]”

Any idea? I thought i have changed it to 587 on the msmtp file.

spenny • April 21, 2014

I got it work. Used the wrong file.php. Apologies

jesse214933 • May 24, 2014

Thank you for this tutorial! It was very helpful and did exactly what I needed!

erwin • July 1, 2014

Hi, followed and successfully configured.

However, its rather slow even for the test mail. Takes 3-5 mins, is it normal?

Kamal Nasser

DigitalOcean Employee

• July 1, 2014

@erwin: What’s the latency between your server and the SMTP server you’re connecting to?

ping -c 4 smtp.mail.yahoo.com

ping -c 4 smtp.gmail.com

erwin • July 2, 2014

Ok … managed to nail the problem, droplet is in Singapore 1 with IPv6 enabled. It takes 3-5 minutes with IPv6 and after disabling IPv6 within OS (nothing else changed), it takes 2-4 seconds with IPv4.

I do not know if it is Google or DigitalOcean but I really hope that DigitalOcean will look into and check if there is a IPv6 routing or speed issue.

soniclover • August 23, 2014

msmtp: TLS handshake failed: An unexpected TLS packet was received. msmtp: could not send mail (account gmail from /home/pi/.msmtprc)

I have no idea what this means, could someone help? I would greatly appreciate it!

Emad Alghamdi • September 16, 2014

When I run the test php command it throws this error.

sh: 1: /usr/sbin/sendmail: not found

Why is it even setting it to sendmail path? how can I change it to make it use the msmtp? Also it’s not logging this error. I had to run the php in putty to get this error msg =\

Please help

Jesin A • September 16, 2014

If you run php scripts from the command line the following configuration file is used:

/etc/php5/cli/php.ini

So you have to make those changes here.

Emad Alghamdi • September 16, 2014

Thanks jesin. I did the change to the apache2 php.ini so thanks for pointing out that its in the cli folder. Ok it sent the email successfully through putty but when trying to run it through the browser it gives an error. Problem if I go to the log now it just shows the one that got sent.

UPDATE It’s loggin under Apache2 though: msmtp: /etc/.msmtp_php: Permission denied

Emad Alghamdi • September 16, 2014

I have allowed myself to change it but now it gives this msg.

msmtp: /etc/.msmtp_php: must be owned by you

Jesin A • September 16, 2014

You’re welcome!

It must be owned by the user under which the Apache/php5-fpm process is running.

This could be www-data or apache2. Try changing the file’s ownership to one of them and also chmod this file to 600.

Emad Alghamdi • September 16, 2014

This comment has been deleted

Emad Alghamdi • September 16, 2014

www-data worked! Thank you!

Emad Alghamdi • September 16, 2014

One last question.

How can I make it work with my process.php for my contact form? It’s using phpMailer.

Example masked. Appreciate your help.

<?


$body = ob_get_contents();



$to = 'someone@domain.com';
$email = $email;
$fromaddress = "me@domain.com";
$fromname = "Online Contact";

require 'library/PHPMailerAutoload.php';

$mail = new PHPMailer();

$mail->From     = "me@domain.com";
$mail->FromName = "me@domain.com";

$mail->AddBCC("me@domain.com");

$mail->AddAddress($email,$name);

$mail->WordWrap = 50;
$mail->IsHTML(true);

$mail->Subject  =  "domain.com (Contact Form)";
$mail->Body     =  $body;
$mail->AltBody	=  "Thank you for contacting us"; 


if(!$mail->Send()) {
	$recipient = 'me@domain.com';
	$subject = 'Contact form failed';
	$content = $body;
	
	
  mail($recipient, $subject, $content, "From: me@domain.com\r\nReply-To: $email\r\nX-Mailer: DT_formmail");
  exit;


}
?>

Jesin A • September 16, 2014

PHPMailer can be used to directly send emails via SMTP. Add these before $mail->Send():

$mail->SMTPAuth   = true;                  // enable SMTP authentication
$mail->SMTPSecure = "tls";                 // sets the prefix to the servier
$mail->Host       = "smtp.example.com";      // the SMTP server
$mail->Port       = 587;                   //the SMTP port for the server
$mail->Username   = "yourusername@example.com";  // username
$mail->Password   = "yourpassword";            // password

Emad Alghamdi • September 16, 2014

They were there already and tried to send with it and didn’t work so I removed them assuming it will use the settings in the msmtp but still, didn’t work. =\

Jesin A • September 16, 2014

Enable debugging with the following code:

$mail->SMTPDebug  = 4;

See what you get without the SMTP settings and with them.

Luk3 • September 25, 2014

I’m having the same issue as dmmd running CentOS… Everything works up until I try to send the test email.

[root@first msmtp-1.4.32]# cat sample_email.txt | msmtp --debug -a yahoo bob@domain.com ignoring system configuration file /usr/local/etc/msmtprc: No such file or directory loaded user configuration file /root/.msmtprc using account yahoo from /root/.msmtprc host = smtp.mail.yahoo.com port = 465 timeout = off protocol = smtp domain = localhost auth = choose user = myUserName password = * passwordeval = (not set) ntlmdomain = (not set) tls = on tls_starttls = off tls_trust_file = (not set) tls_crl_file = (not set) tls_fingerprint = (not set) tls_key_file = (not set) tls_cert_file = (not set) tls_certcheck = off tls_force_sslv3 = off tls_min_dh_prime_bits = (not set) tls_priorities = (not set) auto_from = off maildomain = (not set) from = myUserName@yahoo.com dsn_notify = (not set) dsn_return = (not set) keepbcc = off logfile = (not set) syslog = (not set) aliases = (not set) reading recipients from the command line msmtp: support for TLS is not compiled in

Any suggestions? I already had the tls_certcheck set to off.

Thanks.

Jesin A • September 28, 2014

I guess you need to install OpenSSL and then reinstall MSMTP.

yum remove msmtp
yum install openssl
yum install msmtp

fatbat • October 23, 2014

Thank you for this. Skipped sendmail for this. However I would suggest not disabling TLS cert check.

Run this command to find cert issuer of your SMTP host.

Then simply locate appropriate cert to be used by msmtp.

tls_trust_file /usr/share/ca-certificates/mozilla/Thawte_Premium_Server_CA.crt
domain yourdomain.com
port 587
keepbcc on

Now I just need to figure out how to use passwordeval + gpg with this so password is not plaintext.

montefuscolo • October 30, 2014

It works for me exactly as described. I’m using an Archlinux and msmtp in version 1.4.32.

Thanks, it’s very useful.

jeff781158 • November 19, 2014

I get to the part to enter my data into vi ~/.msmtprc however I cannot figure out how to save it and move to the next screen. Im a total noob with the terminal. Please help someone :)

jeff781158 • November 19, 2014

nevermind I figured this one out

jeff781158 • November 19, 2014

i am getting “The program ‘php’ is currently not installed. You can install it by typing: apt-get install php5-cli”

I have the current LEMP stack installed

Jesin A • November 19, 2014

That is exactly what you have to do:

apt-get install php5-cli -y

jeff781158 • November 19, 2014

When I run php /var/www/html/file.php I get this in the terminal"Could not open input file: /var/www/html/file.php". The email sends if I send it from the terminal but no through the mail script, I also get a 404 error when I try to view the file.php in the browser

j c • November 23, 2014

HI, i’m having a problem with this. It was going ok until I tested in the browser and it did’nt send a email, now i’m getting this message back /usr/bin/msmtp: invalid option – ‘c’ when I run php /var/www/html/mailtest.php on the command line, Any ideas how I can sort this…

Kamal Nasser

DigitalOcean Employee

• November 23, 2014

@Razor303: Make sure that the C is in uppercase:

sendmail_path = "/usr/bin/msmtp -C /etc/.msmtp_php ...

not

sendmail_path = "/usr/bin/msmtp -c /etc/.msmtp_php ...

Don’t forget to restart Apache or php5-fpm after updating php.ini.

Jesin A • November 23, 2014

@jeff781158 If you see a 404 error on the browser the wrong file is being edited. Are you using Apache or Nginx?

j c • November 23, 2014

@kamain7 thanks dude, I can’t believe I missed that. anyway it’s worked with php from the command line I’m ssh in to my server from my phone when I get home I’ll test it properly, but it’s looking good

j c • November 24, 2014

@jeff781158 i’m using Apache2 at the min ! but i will be using Nginx when I move from testing, tinkering & developing to production. I’m not getting a 404 error, it sends it ok with php on the command line but not from the browser, php echo’s An error occured from the sample script. I haven’t got a domain name yet because i’m testing that wouldn’t matter, would it? below is the php script i’m using

<?php if(mail(“myemail@gmail.com”,“Test messsage”,“Hi there Sh*t it worked !,\nThis email was sent using PHP’s mail function.”)) print “Email successfully sent”; else print “An error occured”; ?>

I have saved the file as index.php in /var/www/html then in my browser I put servers-ip/index.php

Kamal Nasser

DigitalOcean Employee

• November 24, 2014

@Razor303: What OS are you running? You might need to edit a different php.ini file depending on where the distribution’s packages store the configuration files by default. Are there any errors in /var/log/mail.err?

j c • November 24, 2014

@kamaln7 i’m using Ubuntu LAMP on 14.04. had a look in mail log there are a few entries because i’ve been sending a lot of test email some end with EX__OK they must be from the php command line because I can send mail from there, there are also some ending with --Header:

EXAMPLE BELOW:

[23-Nov-2014 23:37:08 America/New_York] mail() on [/var/www/html/index.php:2]: To: Myemail@gmail.com – Headers:

Jesin A • November 26, 2014

@Razor303 Must be a problem with the permissions. Check who owns the config file: