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Hi @Shawn Stoyer ，
What's the specific vesion you are working with and would like to upgrade(File>Office account>About Outlook)?
Outlook 2014 to Outlook 2019
As I know, there seems to be no version 2014 and 2019 in update history of Microsoft 365, if you actually would like to working with Office 2019 instead of Microsoft 365 client, we need to uninstall Microsoft 365 and re-install the Office 2019.
If you just would like to update to any version of Microsoft 365, we could update it directly in Outlook via File>Office account>Update Option>Update now
Hope that would be helpful to you.
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