Hi @Joseph Ochoa ,
Welcome to our forum!
According to your description, i notice that the issue occurs on Outlook desktop client and Outlook on web, i'm afraid that the issue is more related to your account. Does this issue occur when you send all emails to your wife's hotmail.com account or a specific email?
In order to further confirm the issue, you can send emails to other Outlook.com accounts to check if the issue persists. If the issue only occurs with your wife's hotmail.com account, you can try to add your personal account to the safe sender of your wife's hotmail.com account.
If the above doesn't help, 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.
Thanks for your understanding and support!
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