When trying to send emails from your site to yourself, it's recommended to use a third party service like Postmark, Mandrill, Sendgrid or a similar service to avoid email failures. These services require, or at least strongly, suggest adding Headers to your server to say you're authorized to send them. When email clients such as Gmail sees these, it'll likely send them to spam, or possibly even stronger protections resulting in not receiving them at all. In addition, another suggestion would be to use something other than the admin email address like firstname.lastname@example.org to avoid potential failures.
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