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Are you aware of a tool that I could use to craft a longer path? Most lightning wallets I tried use automatic routing algorithms that select the shortest path or the lowest fee. I never found a way to configure different behaviors.
How do you go about learning which nodes should I trust on the network? The only practical way I see is to personally know the "entry" node, which basically means owning it. Should I spin up a public decoy node to route all my transactions through in order to be sure that at least one node will never give away my privacy?
I am no expert on lightning software so I am not aware of a tool but it probably exist. Something like letting you choose your first few hops and then the automatic routing takes over from there would be good.
Trust would have to be established traditionally through social relationships. Very trick currently because of how small bitcoin is.
A node you own to route your payments through would not help much because lightning currently uses HTLCs to secure it payments. HTLCs make it so every node your payment goes through has an identical token. Nodes colluding to attempt to de anonymize payments can identify a single payment flowing through the various nodes by this token. PTLCs is an alternative to HTLCs that is being worked on and should fix this.
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