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I had a few issues with this when Win10 was in the trial phase, as I'm on the insider programs for the OS.
From my understanding of the discussions I had with LW techs at the time, there is a particular unique key that Hero Lab looks for to confirm that the copy of windows it is installed on is the one expected by the license, which changes when you change Windows versions. I believe from memory that it has been sorted so that it won't cause issues with normal Windows updates, but it is still an issue if altering Windows version or on the Insider Program because they effectively install fresh copies of Windows with new unique keys.
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