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When you use a VPN can your OS update request be used to de anonymize you? I would think that Microsoft or Apple would get a request saying "the OS running on this machine with activation token 0xfe875c56a788d0 is checking for an OS update" regularly, so that the government could subpoena for the activation token held by the device that had IP 164.21.13.112 at 7pm on March 25, and then for all other IPs that this token has ever requested OS updates from.

Do Not Use BitTorrent should be numero uno.

Why? I don't think BitTorrent is actually a privacy threat, for the most part, it would just put undue load on the Tor network if everyone were doing it.

Because of the protocol your real IP is likely to be leaked.

Interesting - it seems that the more measured (privacy) advice should be: "don't use BitTorrent unless you know that your client implements the protocol in a privacy-protecting way". It seems that the protocol itself is not to blame, but the way it is implemented in many (most? all?) clients leaks significant identifying information. See here: https://blog.torproject.org/blog/bittorrent-over-tor-isnt-go...

Do not spend bitcoin you bought in the clearnet when purchasing non legal materials from the darknet

Things not to do when anonymous