You can't easily know ahead of time of there's a path to the receiving peer. Can't make a payment if there isn't one.
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Does that happen frequently? Which peers don’t have paths to them? Is it an issue of the receiving peer not managing their liquidity, or the sender not finding a route? I noticed that Lightning payments have become more expensive over time (~2500ppm now), but if you’re willing to pay that, there always seems to be a route