Impervious did something similar a long time ago
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From what I could tell, their implementations only boostrapped a connection using keysend, then sent the rest over a traditional way. It didn't seem like they did the actual data transmission over keysend, did they? Their documentation was very weak and now is not even available from their homepage, you have to google search for it.
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IIRC in their initial implementation they did it like this, then switched it to just the bootstrapping. @tonygiorgio would know better tho
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There was a few different ways to achieve bigger payloads. One was by initiating some handshake for a different protocol. But the keysend like one, we used AMP to essentially be a MPP-like keysend payment where each part had different bytes and it either all made it to the recipient or none at all. Added atomicity to the data payload.
If you're just sending out a bunch of keysends, you have to consider the fact that one might not make it or ever make it. You wasted sats for a broken payload if the rest made it.
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