Windows 10: I am forced to "Troubleshoot" Windows 10 Pro Activation every single day

Almost identically to this thread from a month ago, basically ever single day around the same time, I get the little overlay in the bottom-right corner telling me I need to activate Windows. And every single time, I have to go here and hit Troubleshoot. It's successful every single time. But then I just end up having to do it again the very next day.

I run a dual Pihole setup on my network. Naturally, that was one of the first things I checked. So I temporarily disabled both Piholes. Then on my computer I ran ipconfig /flushdns and shutdown my computer for the night. The next day, I disabled both Piholes again before booting up my computer. I kept them disabled for most of the day until, once again, I saw the overlay warning me that Windows wasn't activated. So that completely eliminated the Piholes as being the cause of the issue.

At this point, I'm at a complete loss as to what to try next. I just built this PC a few weeks ago (my first desktop PC I've ever owned, let alone built) and it's been pulling this crap since the day after I installed Windows for the first time.


Edition Windows 10 Pro Version 1909 Installed on 4/10/2020 OS build 18363.778
submitted by /u/misterpyrrhuloxia
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:)

 

Windows 10 Activation (Insider)

How long did you wait for activation?
When I re-installed with a fresh install... it took a few hours to sync and activate.
However, it did, finally, activate.

 

Windows 10 Activation (Insider)

Hi!

I signed up in the windows insider program and got windows 10 free - the windows 10 insider preview updated to windows 10 pro.
Today i got another SSD and did a raid 0 on my system forcing me to do a clean install of windows but now it wont activate anymore.
Signing in with my microsoft account that was linked to the insider program didnt help.
Maybe i got this problem since i quit the insider program for several days and signed up again after i found out that my win 10 wont activate anymore.
Any ideas how to fix it?

Lauri

 

Windows 10 Activation (Insider)

I bought Windows 7 Pro OEM key from G2Play.net for 12€ to upgrade to Windows 10 Pro - worked like a charm but be advised if you buy a OEM key you can not download the Win 7 iso from microsoft and have to get it elsewhere.