Error when requesting password reset email – wp authentication

Sounds like a server configuration problem, not a WordPress thing. You said you were using Rackspace? I don’t have personal experience with Rackspace but it appears that they have some known issues with the default PHP mail() function. See:

  1. http://feedback.rackspace.com/forums/71021-product-feedback/suggestions/1873281-fully-support-php-mail-function-
  2. http://www.joshuawinn.com/huge-email-delays-on-rackspace-cloud-sites-dont-use-php-mail/

The primary issue is that sending straight through mail() doesn’t authenticate the sender, using open relays, which is something that could be abused and seems that Rackspace delays or doesn’t support well. That’s what it’s not working as you’d normally expect.

Great first step in trying to use an SMTP plugin, as that is the commonly accepted workaround. If PHPMailer is giving you problems, it may be an issue with the original configuration. You can also try port 465 using SSL instead of TLS, which is often the biggest issue. Also, are you using any extra security mechanisms from Google, such as two-factor auth or application-specific passwords? That’s another thing to watch out for.

If you have any other details or evidence do share.

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