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Genuine question: is there a possibility that Monero is being monitored covertly?

It seems an obvious target to be a Trojan horse in the midst of criminals and tax-evaders.

It is possible but unlikely. It is likely that clearnet use of monero is monitored, for example. But in terms of security, monero users are very cautious. The code has been independently audited, and has generally succeeded where other cryptonote-based cryptocurrencies have taken fatal missteps.

I suspect that most monero black markets are taken down by sting operations. The black markets all have a limited shelf life and these days they tend to intentionally retire before getting "silk-roaded"

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