3 ms·

I don't think the real problem with OpenPGP is the UI issues. OpenKeychain and K9-Mail together provide a not terrible UI for OpenPGP, and if someone wanted to

I don't think the real problem with OpenPGP is the UI issues. OpenKeychain and K9-Mail together provide a not terrible UI for OpenPGP, and if someone wanted to more tightly integrate them with each other,the UI could probably be improved further. But PGP-over-SMTP would still leak important metadata, and you would still have problems with forward secrecy and key revocation. Matrix looks like a much better decentralized solution to build a new email infrastructure on. But there are still metadata leakage issues with federation, and there need to be some standards and an example implementation for email-over-matrix.

lmm 10y ago
> But PGP-over-SMTP would still leak important metadata, and you would still have problems with forward secrecy and key revocation. I don't think a well-integrated PGP-over-SMTP client would leak any more metadata than the likes of Signal does? Build in a good subkey rotation config and you'd solve most of the forward secrecy issues, and good defaults for how to treat revocation (including better expiry defaults) would resolve that issue. No?
- NoGravitas 10y ago
  You would still leak unencrypted headers, which in SMTP are numerous and interesting. A client could minimize the useful content of the message headers, but you're always going to have at least the envelope headers available to every intermediate mail host. I do not know enough to be sure about your point about forward secrecy. You may be right.
  - e12e 10y ago
    Depends a bit what one considers integration: https://en.m.wikipedia.org/wiki/Anonymous_remailer https://en.m.wikipedia.org/wiki/Anonymous_remailer
  - lmm 10y ago
    > you're always going to have at least the envelope headers available to every intermediate mail host. Sure, so any intermediate server would see who was talking to who. But that's the case with Signal et al as well isn't it?
    - NoGravitas 10y ago
      Currently, yes.
    - cpach 10y ago
      ”But that's the case with Signal et al as well isn’t it?” No. ”Because your phone will be connecting to Signal’s servers, your cellular carrier can determine whether or not you are using the service. However, your carrier cannot gather any information about the individuals or groups with whom you are communicating.” Source: https://github.com/WhisperSystems/Signal-iOS/wiki/FAQ#what-about-metadata https://github.com/WhisperSystems/Signal-iOS/wiki/FAQ#what-a...
      - lmm 10y ago
        Right, but Signal's servers see who you're communicating with, and they're the equivalent of the intermediate mail servers here.

lmm 10y ago

> But PGP-over-SMTP would still leak important metadata, and you would still have problems with forward secrecy and key revocation. I don't think a well-integrated PGP-over-SMTP client would leak any more metadata than the likes of Signal does? Build in a good subkey rotation config and you'd solve most of the forward secrecy issues, and good defaults for how to treat revocation (including better expiry defaults) would resolve that issue. No?

NoGravitas 10y ago
You would still leak unencrypted headers, which in SMTP are numerous and interesting. A client could minimize the useful content of the message headers, but you're always going to have at least the envelope headers available to every intermediate mail host. I do not know enough to be sure about your point about forward secrecy. You may be right.
- e12e 10y ago
  Depends a bit what one considers integration: https://en.m.wikipedia.org/wiki/Anonymous_remailer https://en.m.wikipedia.org/wiki/Anonymous_remailer
- lmm 10y ago
  > you're always going to have at least the envelope headers available to every intermediate mail host. Sure, so any intermediate server would see who was talking to who. But that's the case with Signal et al as well isn't it?
  - NoGravitas 10y ago
    Currently, yes.
  - cpach 10y ago
    ”But that's the case with Signal et al as well isn’t it?” No. ”Because your phone will be connecting to Signal’s servers, your cellular carrier can determine whether or not you are using the service. However, your carrier cannot gather any information about the individuals or groups with whom you are communicating.” Source: https://github.com/WhisperSystems/Signal-iOS/wiki/FAQ#what-about-metadata https://github.com/WhisperSystems/Signal-iOS/wiki/FAQ#what-a...
    - lmm 10y ago
      Right, but Signal's servers see who you're communicating with, and they're the equivalent of the intermediate mail servers here.