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The silk road did work like an escrow where SR would hold the bitcoins until the buyer finalized (FE for short). Bitcoin would have an internal tumbler that would generate multiple addresses and would make it difficult to track the transactions.

Most vendors would ask for early FE or no product would be shipped but that was too risky for most buyers. FE was supposed to occur when the buyer received the product and gave it thumbs up.

How was a trust relationship built?

I could assume that major vendors with high ratings could do early FE as their means, but would unrated vendors have to essentially front and hope that the buyer would FE?

Was the FE ever automated based upon FedEx/UPS tracking numbers?

That would seem like a bad idea because then the receivers address would have to be within the SR database

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