Hi @Mike McCord ,
Thanks for your reply!
I think you can create a rule to forward all emails received in Outlook.com to your Gmail account via Settings>Mail>Rules:
If it doesn't work, considering that your issue is more related to your Outlook.com account and the auto-forward feature, please kindly understand that the Outlook tag here we mainly focus on general issues about Outlook desktop client. It's suggested that you could post your case in dedicated forum for Outlook.com for more professional advice.
Thank you for your understanding and support!
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