Good evening William and welcome back!
Thank you for reaching out to us.
We are sorry to hear about the emails not making it through to outlook.com
I would love to help you with this topic.
What is probably going on is that all of the microsoft family email clients are known for being extra picky when it comes to receiving emails.
You can have the system send tickets from any chosen email address by simply installing, configuring and testing the following plugin: https://wordpress.org/plugins/easy-wp-smtp/
Using a real SMTP server with authentication will bypass the built-in WP mail functionality altogether.
Please make sure you configure and test the settings using the plugin’s built-in tool.
If that does not work properly, you might have to add DKIM records to your domain for Microsoft to let the emails in.
Let me know how that goes.
Best regards,
Geoff B.