Agreed... having anonymity set of 1000 doesn't help you if someone has enough resources to interrogate 999 people.
Yeah, or issue those dragnet surveillance court orders that can easily target 999 people at once. But I think the whirlpool anonset is larger than 1000, and how does mixing multiple rounds affect it?
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One round is at most x5, so 2 rounds are 25, 3 rounds 125, 4 round 625...
(it's a bit more complicated and the details of the transactions matter, some people will send multiple utxos, some people will mess up after, etc)
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Yeah there are x5 outputs in a mix, but there are also 5 inputs. At least 3 inputs, but up to 4, are premix and at least 1, but up to 2 are remixers. So I don't think it's as simple as your math.