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Not sure if this is wordpress or woocommerce-specific but I've run into an issue where emails aren't being sent out if the FROM email is my personal gmail.

According to WP Mail Logger, emails were sent out with no errors in all instances. It's funny that the third email actually gets sent out, given that I have no control over blahblahblah.co although it does seem to be registered

Is this a gmail security thing? I do find it kind of suspicious that I'm able to enter completely random emails and claim to send emails from them, but how would I debug this issue?

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Most recieving mail systems will reject an email with a 'from' of [email protected] when the email is sent from the mydomain.com system. This is to prevent mail relaying, a form of spam.

You need to make sure that your 'from' email address matches your domain. The actual email address (like [email protected] for mydomain.com) doesn't need to exist, but the mydomain.com in the email must match the mydomain.com domain name of the sending mail server.

You can always set the 'reply-to' of an email as [email protected], and that mail will be delivered through yourdomain.com mail server. That allows someone to reply to your gmail account.

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  • Thanks for the response. That's generally my understanding of what mail servers would do with mismatched domains, so it was interesting to see that emails sent from [email protected] actually went through. Maybe gmail is just selective about what's considered mismatched domains.
    – MxLDevs
    Commented Oct 30, 2020 at 0:36

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