I guess the simplest way is to run cmd tool that is responsible for updates and check if it fails to update (error code or error message returned) your system. However you should be prepared to the fact it can take your system to undesirable state which will require roll-back.
To have more "reliable" and "proper" ways you need to know what OS you are ...
There are OS that force updates and others and won't update unless you act.
The latter is naturally not a problem.
For the former, I see two options:
1 - You can run inside a Virtual Machine, using VMWare e.g. Probably you will need to refactor the data migration.
2 - You can monitor the version using some script that run by a CRON job. In Java, e.g., ...
Instead of running the click straight away you can iterate over the results and see if they are suitable before clicking them.
foreach (button in self.driver.find_elements_by_name("button_name"))
if button.property == 'what i want'
You can add other constraints on the button by adjusting the if statements.
Nothing inside the ...
Katalon Studio supports Windows 10 application testing. From v 7.0 (currently in beta).
I belive it is Winium based.
More info here: https://docs.katalon.com/katalon-studio/docs/introduction-desktop-app-testing.html#windows-execution-type.