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The problem is not encryption, S/MIME works well enough for that.

The problem is you don't have public keys for people you send to.

And there's not a reason for many to get the keys.

I wish I could say "I'll read your unencrypted email tomorrow" (and delay it from getting to my inbox).

S/MIME actually solves the key problem pretty nicely, every signed mail contains the certificate that is required to send an encrypted reply. Just start signing your mails.

That's just the TOFU/POP trust model, same as unverified SSH server keys. Doesn't help against persistent MITM.

Sure it does. The information in the certificate is signed (by the intermediate CA) and will contain a certificate chain that leads to a trusted CA and the email address and possibly even the subject's name will be encoded within the certificate. If you can trust the root CA, you can trust that the other party is who they say they are.

Then we get to argue whether NSA can get bogus valid certificates from the commercial CA's... Of course you could roll your own CA but then both parties need to trust it.

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