I had issues with updating my PC (Win 11), and figured out it's due to a change in a adress required by the Windows insider program: insideruser.microsoft.com
Whitelisted now, if you have similar issues fyi.
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As of today, that domain appears on one public blocklist.
https://blocklist-tools.developerdan.com/entries/search?q=insideruser.microsoft.com
Was this domain being blocked by your Pi-hole?
Yes indeed blocked by my pihole.
Blocked (gravity, CNAME)
The domain itself was not blocked, but it led to a CNAME that was blocked. By whitelisting the domain, you are telling Pi-hole to not block that domain regardless of where the CNAME leads.
Strange thing is that it isn't always blocked.
Or isn't it strange? Will read some on how CNAME works.
It's not clear why the domain was blocked sometimes, and not other times. Perhaps changes you made to your whitelist between queries?
For this specific domain, here is the CNAME trail:
dig insideruser.microsoft.com @1.1.1.1
...
;; ANSWER SECTION:
insideruser.microsoft.com. 3600 IN CNAME insideruser.trafficmanager.net.
insideruser.trafficmanager.net. 300 IN CNAME flightinguserauth-eus.flighting-prod-ase-eus.p.azurewebsites.net.
flightinguserauth-eus.flighting-prod-ase-eus.p.azurewebsites.net. 30 IN CNAME waws-prod-blu-ebaea57f.sip.p.azurewebsites.windows.net.
waws-prod-blu-ebaea57f.sip.p.azurewebsites.windows.net. 1800 IN CNAME waws-prod-blu-ebaea57f.cloudapp.net.
waws-prod-blu-ebaea57f.cloudapp.net. 10 IN A 13.92.153.50
No I didn’t make any changes in between. Only after I figured out it was that domain i whitelisted it. Well, my problem is solved at least 
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