Hello Tyler McKnight,
Thank you for posting in Microsoft Community forum.
Yes, it is recommended to put the Windows Terminal Server into Install mode before installing monthly Windows updates. This is because the Install mode ensures that the updates are installed correctly and that any necessary changes are made to the system. Install mode is also required when installing or updating an application on the server. It is important to note that you should ensure there are no connected users before patching and follow the proper process to avoid any potential issues.
I hope the information above is helpful.
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Best Regards,
Haijian Shan