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I agree that many articles are a little too glowing on the anonymous aspect, but the level of anonymity you have with any system is proportional to your sophistication, so I don't see it as a problem inherent in bitcoin. See https://en.bitcoin.it/wiki/Anonymity for more info on the anonymity of the current bitcoin implementation and system.

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Thanks for the link, and well said that anonymity is basically always proportional to sophistication. What worries me is that other, related systems people will have experience with (like anonymous file-sharing, public-key encryption, onion routing) have many fewer hoops to jump through to feel confident that they're working correctly. Apples to oranges, but expectations work like that.

If I throw a disk containing my 2048-bit private key into a fire, I can be confident that nobody is ever going to decrypt my files. Getting the same level of confidence for Bitcoin anonymity is a lot tougher.

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