I think you'll find this has been solved for years. The solution is PGP/etc. between mail servers, and TLS/SSL to the user.
Given that I've seen PGP-signed spam mails, no, I think you're being naive.
Solutions like GoodCrypto integrate with your existing mail server.
Then I don't want it. If you're running the mailserver and you can decrypt my secured messages, then there's nothing preventing the federal government from serving you with a subpoena saying, "please hand over the encryption keys."
The only person who can be trusted to do the decryption is the end user, running on hardware the end user directly controls.
This solution doesn't block experts who prefer user-to-user encryption, but an organization may object for the reasons that you gave, Robert.
I care very little about what happens to corporations. You're still talking about destroying the antispam experience of end-users. That's what I have the biggest problem with.
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