Reduce the risk of email rejection by making WordPress on Symbiosis Wheezy send emails via SMTP if DKIM is configured


#1

I recently migrated yet another WordPress installation from a Turnkey Linux install to join my others on Symbiosis wheezy. As I’ve briefly mentioned elsewhere, this went without major problems.

I also decided to configure SPF and DKIM as part of my plan to finish migrating mail services over. However, I didn’t consider the fact that this has an impact on the deliverability of emails sent from WordPress and presumably other similar PHP-based web applications.

I’ve been using a catch-all forwarding rule and spotted a rejected email from Yahoo! Mail. The rejected email was a blog post that was shared by email using WordPress JetPack sharing. The rejection notice quoted 554 5.7.9: Message not accepted for policy reasons. The explanatory URL clarifies:

Your email failed one or more of the following industry-wide authentication checks that Yahoo uses to verify emails are truly sent from the domains they claim to originate from.

It goes on to briefly explain DKIM, SPF and DMARC (NB DMARC is not currently implemented in Symbiosis).

Thankfully, this is a solvable problem - in fact, it’s not even really a problem, as Yahoo! Mail is just doing its job by checking for correct DKIM headers.

However, WordPress doesn’t make solving it obvious. Chad Butler has done a ton of investigation into WordPress’s email woes, pointing the finger at the wp_mail function - a “wrapper” for phpmailer. The solution is to force WordPress to use SMTP via phpmailer. Here are two suggested approaches:

  1. Edit your theme’s functions.php to include an extra code snippet that configures WordPress to use SMTP to send email.
  2. Use an extra plugin to bring this functionality to all themes and WordPress email functions. Chad recommends WP Mail SMTP which I’ve just deployed and tested briefly with WordPress 4.0.1 (this may useful for multi-site setups too).

With both approaches, there are some Symbiosis-specific things you should be aware of (I’ll use the standard Symbiosis examples here):

  • You need to create a mailbox first, if that isn’t obvious, e.g. blog.
  • The SMTP host is mail.my-brilliant-site.com (on default port 25).
  • The username must follow the example blog@my-brilliant-site.com. Obvious, perhaps, but I always forget this.
  • SMTP requires authentication.
  • I used TLS encryption successfully.

If you’ve tweaked your Symbiosis install to be non-standard, then you’ll have to reflect that here but otherwise it’s pretty much the same as setting up a mail client to send mail.

If you’re using the WP Mail SMTP plugin, then you can send a test email. I recommend trying to send it to a Gmail or Yahoo! Mail address. The result you’re looking for is bool(true) - in addition to the test email of course, which you can examine to ensure it includes the right DKIM-Signature header.

I hope this helps with any head-scratching you might have also been doing!