On Fri, 10 Jan 2020, Rich Shepard wrote:

On Fri, 10 Jan 2020, Paul Heinlein wrote:

The ideal toolchain would I think be something like this.

1. End users generate a keypair (ala PGP) and publish public keys.
2. Bob uses MUA-level hooks to encrypt body of message using Carol's
  public key, signing the message with his private key.
3. MUA submits message to MTA using TLS-negotiated encryption,
  protecting SMTP header info in transit along with already
  encrypted message body.
4. Sender MTA delivers messaage to recipient MTA using similar
  TLS wire-level crypto to protect SMTP header info.
5. Recipient MTA delivers message; body remains encrypted.
6. Carol verifies her trust in Bob's public key.
7. Carol uses MUA-level hooks to decrypt Bob's message using
  her private key and verifying Bob's key as the sender.
  Only the in-memory version of the message is decrypted;
  the on-disk message remains encrypted.

Points 3 and 4 are already in widespread use. Point 5 will always be true is encryption is handled by the MUA.

The lack of a universally accepted key-management system hinders points 1 and 6; I know that's where PGP is aimed, but I'd hardly call it universally accepted.

The closest we have to an MUA standard in points 2 and 7 is S/MIME, which is widely implemented but doesn't work with PGP, relying instead on the same key-management techniques used to issue SSL certificates for, e.g., web sites.

Beyond all that is the problem of data retention. It's likely that a secure system will encourage key expiration, if for no other reason than to keep moving away from once-secure techniques that become insecure due to increased computing power, clever algorithm developments, or whatever. If that's true, what do you do will all the messages that arrived encrypted with your old key?

Paul,

Wow! What an education. Thank you. I suspect that most Windows users would find this overwhelming, and their employers likely not interested.

It's an overwhelming problem regardless of what platform you use. Even for people who put effort into encrypting e-mail, it works only if the correspondent is similarly engaged.

Some employers, however, are actively interested. OHSU, for instance, requires encrypted e-mail for several classes of messages that include HIPAA-protected information. I'm not on that team, so I don't know the extent of compliance or the tech involved, but I know it's a thing.

--
Paul Heinlein
[email protected]
45°38' N, 122°6' W
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