> If the problem in OTR is we can't rely on users to verify who each other are... Not what I'm saying here. I think the specific way they've chosen to verify a

> If the problem in OTR is we can't rely on users to verify who each other are... Not what I'm saying here. I think the specific way they've chosen to verify a new party in OTR -- by agreeing on a shared secret through some other channel -- is a bad user experience with security implications. Normal people will choose dumb, guessable secrets. Or send them over insecure channels. I think the equivalent of an in-person PGP key signing has a better chance of succeeding. If we're talking about an app, one person's phone could display a QR code of their pubkey, and the other could scan that in to import it. As with PGP, once the web of trust has a backbone (composed of hardcore early adopters like us here on HN), you can skip the in-person step, and trust keys that enough of your contacts trust. OTR doesn't have this network effect. > The only solution to it is external trusted parties. Sure. But who those external trusted parties are is the crux of the issue. Is it a browser maker and a couple companies you don't get to choose? Who are perhaps cooperating with some government (hey, it's happened)? Or is it people you actually choose and choose to trust? > On top of that, PGP is exactly a step backwards if you're worried about just observation of metadata because PGP with web-of-trust cryptographically ties every message you send forever back to the key which sent it. I mentioned this in the grandparent: with PGP, you could also derive ephemeral keys for the conversation, as OTR does. > You have to choose which problem you find more important: either you can be very anonymous, or very sure of who you're talking to but never both. Not so. You can both be anonymous from the man-in-the-middle's perspective, but can also verify each other. Look at how OTR does it. The "Socialist Millionaire's Protocol." http://en.wikipedia.org/wiki/Socialist_millionaire http://en.wikipedia.org/wiki/Socialist_millionaire