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.

I ended up going down a deep rabbit hole of apparmor permissions, etc.

Here’s my recommandations:

• Check /var/log for last modified file when you execute the PHP script to see which files are logging errors
• Run the PHP script in CLI as www-data (or whatever your webserver runs as), since it gives more detials than just “an error occurred”:

sudo -u www-data php mail.php

In my case, these were the changes needed:

sudo nano /etc/apparmor.d/usr.bin.msmtp

Then add:

/etc/.msmtp_php r

Reload apparmor:

sudo apparmor_parser -r /etc/apparmor.d/usr.bin.msmtp

sudo chmod 600 /etc/.msmtp_php

Good luck!

Had the same issue with PHP 8.2 of emails sending in SSH, but not from the PHP file itself. Nothing in the logs.

Ultimately gave up and just decided to send emails like this:

exec('echo -e "To: alice@email.com\nSubject: Your subject \n\nYour message body" | msmtp -a gmail bob@email.com');

Thanks for the awesome tutorial! I have found tons of new and useful information here and it worked.

I’m close to getting this working, but can’t get the last step. This line sends the email just fine:

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

But when I try to execute it from a php file (either in the command line with “php /var/www/file.php” or in the web browser) it doesn’t send at all. Oddly, the command line returns “Email successfully sent” while the web browser says “An error occurred.” It seems like something is wrong with the php config. Any ideas?

Five years later and this article is still helpful. Incase anyone else is still reading and has any issues like with security warning, follow these steps:

1. Setup HTTPS
2. Setup UFW with correct ports
3. Create an secondary email account (name it something like auto.response@gmail.com).
4. Set PHP mail headers as follows:

  mail ( $to, $subject, $html_email, getMailHeaders() );
  function getMailHeaders() {
    $headers = "From: No-Reply <example@gmail.com>\r\n";
    $headers .= "Return-Path: Name <example@gmail.com>\r\n";
    $headers .= "Bcc: Name <example@gmail.com>\r\n";
    $headers .= "MIME-Version: 1.0\r\n";
    $headers .= "Content-type: text/html; charset=iso-8859-1\r\n";
    $headers .= "X-Priority: 3\r\n";
    $headers .= "X-Mailer: PHP". phpversion() ."\r\n";
    return $headers;
  }

Following these steps all emails have no security warning and are not marked as spam.

Hi,

first of all thanks for this and all the other great tutorials!

However, with this one I have one issue I could not solve.

If I do: cat sample_email.txt | msmtp --debug -a gmail bob@domain.com

There is a lot of console output, ending with: reading recipients from the command line

If I wait long enough (approx. 2 minutes) I receive the mail. However, the problem propagates to phps mail function. This means, if a user fills out a contact form he has to wait for approx. 2 minutes until he receives feedback.

(When googling, I usually find that the /etc/hosts file needs to be properly set, however, this is not the issue here).

Any ideas?

Excellent tutorial!!! I followed the steps and worked like a charm. But I want to send emails from different senders from my website. eg. If the user goes to www.mypage.com/A.php I want to send a mail from mailA@gmail.com and If the user goes to www.mypage.com/B.php I want to send a mail from mailB@gmail.com

In /etc/.msmtp_php I defined both accounts

account gmailA
...
user mailA@gmail.com
from mailA@gmail.com
password XXXXX

account gmailB
...
user mailB@gmail.com
from mailB@gmail.com
password XXXXX

In sendpath I defined only gmailA

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

and all the mails sends with FROM: mailA@gmail.com Which is fine but I want that sometimes the sender is mailB@gmail.com

I use this headers in mail()

 $header.= "From: mailB@gmail.com \r\n" .
    "Reply-To: mailB@gmail.com \r\n";  

but sender keep being mailA@gmail.com

is there any way to define another account in sendmail_path so I can “choose” which one to use??

Dear All,

I am a newbie and using Debian 8 and NGINX for my web server, just followed this tutorial step by step and finally I still unable to send an email. For testing, I run this command;

cat sample_email.txt | msmtp --debug -a gmail wahyu.wardana@yahoo.com

then I got this message:

-bash: /usr/bin/msmtp: Permission denied

What’s the problem, can you help me, please?

Thank you.

I’ve tried this method. It sends an email with this terminal command “cat sample_email.txt | msmtp --debug -a gmail bob@domain.com”, but when I implemented the mail() in php it does not send. Also, it does not send an error.