Troubleshooting prerequisite, applicability, and installed rules is basically impossible. When a package is not applicable all you get is the generic not applicable error. Then you have to modify the package, delete the old one, publish the new one, possibly sync the downstream server, and run a new Update Management to test again. It would be incredibly helpful if there were a way to test applicability rules against a specific computer from the package creator.
I was thinking something like one button to select a node and one to run the test on the rules pages similar to how you can test components with SAM (I just copy-pasted from SAM for the sample):
The results of the test could tell you which rule it failed on so you can easily tweak the rules until you get the expected result. This ability would make troubleshooting infinitely more pleasant.
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