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 Nostr is good at resisting suppression of public messages

It’s not really designed to be a great private messenger/DM architecture

I know some people were working on better DM stuff on nostr (@hodlbod, others?)

Then there are different architectures/ideas like SimpleX, Keet, and maybe KeyChat coming soon.

What are the best DM/messaging tools today that fully open source, secure, and private? 
 I don't know, but i need one  
 Keet is not open source, simplex integration with nostr would be awesome, there’s also https://github.com/nostr-protocol/nips/pull/1206 haven’t gone through it yet, but looks promising on the surface. 
 @JeffG what’s the story here? 🧐 
 It's basically adapting the signal protocol to work on nostr using relays instead of centralized servers. KeyChat did something on their own but they told me that they based it on Signal as well. 

The double ratchet means that it's both forward (back into the past) and post-compromise (forward into the future) secure, which means, even if your private keys are leaked, the attacker can't read your messages. 

Give me a shout if you want to talk through it. There are still limitations to how good of a UI we can build (yet) but I'm confident it's going to be a huge leap forward for security of nostr DMs. 
 Nice talk today with Odell about this. Was that recorded? 
 Thanks! Yeah. If you look up citadel dispatch on YouTube you should find out. 
 most of keet is open source, and most of the rest you can still view it

https://github.com/holepunchto 
 This is just the protocol though? Is the keet client open source? 
 nostr:nprofile1qyt8wumn8ghj7etyv4hzumn0wd68ytnvv9hxgtcpzdmhxue69uhhqatjwpkx2urpvuhx2ue0qy2hwumn8ghj7un9d3shjtnyv9kh2uewd9hj7qghwaehxw309aex2mrp0yhxummnw3ezucnpdejz7qghwaehxw309aex2mrp0yh8qunfd4skctnwv46z7qgewaehxw309aex2mrp0yh8xmn0wf6zuum0vd5kzmp0qyd8wumn8ghj7urewfsk66ty9enxjct5dfskvtnrdakj7qgwwaehxw309ahx7uewd3hkctcprpmhxue69uhkummnw3ezuendwsh8w6t69e3xj730qyt8wumn8ghj7un9d3shjtnwdaehgu3wdejhgtcqyqtnnkfhmjxqcums4gn4skfccyv7yhzp7mzyrfwnf3kns5p7xymw7y5fhzz  is making the latest foray into doing this on nostr. nostr:nprofile1qy2hwumn8ghj7un9d3shjtnyv9kh2uewd9hj7qgwwaehxw309ahx7uewd3hkctcqyprqcf0xst760qet2tglytfay2e3wmvh9asdehpjztkceyh0s5r9ckfsaet  was a big part of making the latest version of DMs work. I'm also doing private groups on nostr, with all the same trade offs. 
 There is not a lot of privacy if you use SimpleX or Signal with the company's default servers. The servers can see a lot of the metadata. 

That is why I fundamentally think Nostr is better for DMs than anything else. The choice of the DM inbox relay here is at the forefront of the user experience. 

And if you don't trust any server, you can always and easily do P2P DMs in nostr such that the messages never reach any relay.  
 @simplex servers don't see a lot of metadata, no. Maybe IP addresses. 
 IP + channel + date and time of messages + payload size. And if you use the same server for all your contacts (which is what everybody does) then they can see the group of channels you talk to. If both sides use the same server (which is common) the server can map IP to IP, geolocate the pair. Track IP over time and you can isolate work/home locations and from there you can know who the person is, with good probability of sucess.  
 I think we've discussed this before, I think IP protection is the job of another layer.

From what I remember what you have in mind you want a set of nostr relays to perform a sort of mini-Tor routing. Dunno about that how that works and whether that's not the wrong layer.
 
 Sure, nostr could also use extra layers. But COULD doesn't matter. It's either there by default, for everybody, or it's not solved.  
 If you want nostr or SimpleX to solve the IP masking problem then you don't understand tech stacks. We use different solutions for different layers in our tech landscape, instead of bundling layers with apps. 
 Although Nostr was not specifically designed for private notes, its relay model is most suitable for them. Additionally, compared to public notes, private notes face less censorship because they are encrypted. Private notes require less from Nostr's design.