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Email Forwarding - From Gmail to Domain to Gmail

I have setup email fowarding for user@mydomain.com - forwarding to a gmail account. 

 

This works when the original email is sent from an account that is not the original/forwarding destination gmail account. Example:

user@workemail.com - email sent to - user@mydomain.com - forwarded to - user@gmail.com.

However, when sending from inside gmail, it does not work. Example:
user1@gmail.com - sent to - user@mydomain.com - forwarded to - user1@gmail.com

Why is it possible to forward email sent from other email addresses to my domain email but not when the email is sent from a gmail address?

 

Thanks