In general, anonymity systems have huge practical constraints and even things like TOR are subject to various traffic analysis attacks. Privacy is really hard and the best we can do is still vulnerable to some quite practical approaches. TOR for example is reasonably vulnerable to attacks to figure out origin near the origin and to figure out the server near the server. It's reasonably vulnerable to attacks to figure out both if you control enough nodes in the network. Where enough isn't that large if you have some money to throw around. To be clear, the TOR Project is very good at trying to accurately describe what privacy they can and cannot provide.
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