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I am sending the same message through the PHP mail() function using two different addresses in the header. When I send the email with [email protected] it is marked as spam by gmail but when I send the exact same email with [email protected] it goes directly to the inbox. I have tried this with several different messages but with the same results. Does anyone know why the [email protected] isn't being marked as spam but [email protected] is? Would it make a difference that I have an account on the server with the name of admin? Both emails are able to receive mail.

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In general it is not possible to easily determine why a particular message has been marked as spam by the Google Mail spam filters.

Having said that however one item that is an easy test is to check whether [email protected] is in your recipients contact list. Contacts are far less likely to have their emails marked as spam.

You should also review the bulk sender guidelines posted by Google here;

https://support.google.com/mail/answer/81126?hl=en

This contains a whole host of things that you should be doing to ensure your emails are not routinely marked as spam.

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