Hi @Elias Gharib
Thank you for reaching out to the Microsoft Q&A Forum.
I understand you want to upgrade your volume-licensed Office to the latest version, with a focus on getting the newest version of Outlook.
From what I can see, Office 2019 already has the latest security patches.
Please refer the following article: https://learn.microsoft.com/en-us/officeupdates/update-history-office-2019
Therefore, could you please provide more information on what happens when you click the "Update Now" button?
Additionally, could you tell me the current version number of your Outlook? If possible, please also provide a screenshot of your Outlook interface.
Hopefully, the next information you provide will help us find the most appropriate direction to move forward.
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