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So I have had a similar experience. This is how I have solved it. There is a list out there (https://github.com/kevinle-1/Windows-Telemetry-Blocklist/blob/master/windowsblock.txt) that has the list of Microsoft telemetry. However, I have heard from online sources that Microsoft is still able to do telemetry with these blocked. I am not sure how true that is, but I like to play it safe than sorry. Here is what I did to solve the apple problem: little snitch. I know MB talked about it, and I downloaded it yesterday and it works wonders. It blocks all apple and iCloud telemetry off the bat. As for windows, I can’t just tell you to “move to Linux” lol cause it’s not really a good answer or even a solution to your problem. I used this site to update pfsense ( or pfblockerng to be exact) https://linuxincluded.com/using-pfblockerng-on-pfsense/ . The windows list I sent you earlier, I WOULD NOT recommend you manually enter those in the dns blocklist on pfsense. I have tried that, and my blocklist reboot took forever. The better option would be to use the method from the website (2nd link) and then add the website link to pfsense instead of the whole list. I have not tried this one out, so it is uncharted territory, once I do I’ll lyk how it goes. I would say if you put both the blocklist’s of apple, iCloud, and windows on pfsense, you should hopefully be set! I do apologize about the tangent, but just wanted to give you a heads up. Feel free to DM if you have more questions!