Several recent updates from both Microsoft and Apple cause Gig Performer (and quite a few other applications) to “think” that they are running on a new computer. If you have used up your three activations and you did not deactivate Gig Performer beforehand, you may end up being unable to reactivate Gig Performer again. See this KB article for more information.
Are you recommending that I de-activate all my plugin licenses before updating my Windows 10 laptop (in addition to the GP license)?
We are only talking about your Gig Performer license. You will need to check with your plugin developers to see their requirements.
I upgraded to Win 10 2009 from 1909 yesterday, with surprisingly few issues so far. I was able to successfully deactivate/reactivate GP (after figuring out which of the serial numbers I’d saved was the right one).
When I updated win10, I only deactivated GP. All my plugins with licenses kept on working.
But maybe some plugins require it. It should be reported on plugin user forum.
@dhj
Warning
As for the last Windows update, Gig Performer license must be deactivated before updating to Windows 10 20H2.
Yet another windows recovery for my part 
I remembered to deactivate and reactivate. I forgot about having to sit through a 30 rackspace load because GP ignores the Shifted Start when the activation window pops up. After activation, GP insists on loading a gig file.
Unfortunately I had not seen this thread. I was just coming on to report the confusion and problems I had… I also had the additional issue of my SL MKII no longer working in GP. after reactivating. When I pressed a note on the SL MKII, the MIDI indicator light in GP would flash, however I would not get any sound. Eventually I found if I “changed” the MIDI input device for the SL MKII to SLMKII again all was well. Thankfully there was an option to do this for all racks. My other keyboards connected to GP were not affected in this way, just the SL MKII
Yes this happen sometimes, that’s why it is interesting to use the Rig Manager.