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Some of the arguments make perfect sense, some do not: > If messages can be sent in plaintext, they will be sent in plaintext. This is not an inherent problem

Some of the arguments make perfect sense, some do not: > If messages can be sent in plaintext, they will be sent in plaintext. This is not an inherent problem with e-mail and can be solved with client software. You can still have unencrypted communication while giving a big red warning if a user sends an unencrypted reply to an encrypted conversation and strip away quotes by default. > Metadata is as important as content, and email leaks it. This is true, but can I do think that this can theoretically be solved be a new generation of server architecture while keeping the federated nature. > Every archived message will eventually leak. The problems here are a matter of implementation and what software is used. > Every long term secret will eventually leak. This is the one inherent problem with PGP e-mail in the entire post as I see it. It is an issue. All the issues the author bring up certainly hold true today but most of them are not inherent to e-mail and I think with enough coordinated effort they can be fixed while keeping decent compatibility. I do think that apart from the metadata issue (not saying that this is to be disocunted!), we could keep using the exact same servers as today in a perfectly secure and private way if we have a new generation of e-mail clients and e-mail cryptography. As for the metadata part: I've been toying with the idea of a messaging system using e-mail for transport but having an encrypted protocol on top of that which solves these issues. It would also require some way of distributing encrypted messages around (maybe in a gossip-like protocol akin to SSB) and broadcasting gateway servers that relay these messages on behalf of large amount of users. Finally, there's something to be said with that PGP was ever only meant to solve the secrecy, non-reputability and integrity of messages, which is only part of a security and privacy story. It doesn't mean that PGP is broken, only that it is incomplete depending on your threat model.

kbenson 7y ago
>> Metadata is as important as content, and email leaks it. > This is true No, it can be true. There are classes of communication where the metadata is really not important. Like when my boss sends me an encrypted email with some secure passwords we don't store in plaintext anywhere. The metadata that shows it's from my boss and might have some identifying is much less important than the fact I don't keep it in plaintext anywhere and it wasn't sent in plaintext, yet I can get to it if needed.
- Legogris 7y ago
  I might have been unclear, I mean what OP is positing under that headline in the article is true. So, the e-mail leaking it part. If you read my whole comment I finish with that it depends on your threat model, which is basically what you're saying.
  - kbenson 7y ago
    Sure, I just think it's worth noting again and calling out explicitly, given that there's a lot of assertions that are being made, but some are only accurate in some use cases. It's either a lack of understanding on the author's side, or a rhetoric tactic that I have little respect for. In either case I think it deserves attention. To some degree, it's not even the threat model which is different, but people's entire use, which of course might change the threat model. The article is treating email as if it's the same as messaging, which it emphatically is not. Email is also the de-facto method of exchanging file for certain types of people (even if it's always been somewhat poor at it), or providing explicit information that should stay around to individuals that isn't desired to be on a website. Email has always been somewhat poor at the use case of instant messaging, but that's okay, it does other things much better than instant messaging (try finding an instant message from ten years ago and migrating it from the service it was on to a new one). Saying that it's not as good as the security models of instant messaging when being used like an instant messager is not a good reason to stop using it entirely. There are other reasons given that are more compelling, but this one seemed to so fundamentally misunderstand what some people use email for that I though it was important to note.

kbenson 7y ago

>> Metadata is as important as content, and email leaks it. > This is true No, it can be true. There are classes of communication where the metadata is really not important. Like when my boss sends me an encrypted email with some secure passwords we don't store in plaintext anywhere. The metadata that shows it's from my boss and might have some identifying is much less important than the fact I don't keep it in plaintext anywhere and it wasn't sent in plaintext, yet I can get to it if needed.

Legogris 7y ago
I might have been unclear, I mean what OP is positing under that headline in the article is true. So, the e-mail leaking it part. If you read my whole comment I finish with that it depends on your threat model, which is basically what you're saying.
- kbenson 7y ago
  Sure, I just think it's worth noting again and calling out explicitly, given that there's a lot of assertions that are being made, but some are only accurate in some use cases. It's either a lack of understanding on the author's side, or a rhetoric tactic that I have little respect for. In either case I think it deserves attention. To some degree, it's not even the threat model which is different, but people's entire use, which of course might change the threat model. The article is treating email as if it's the same as messaging, which it emphatically is not. Email is also the de-facto method of exchanging file for certain types of people (even if it's always been somewhat poor at it), or providing explicit information that should stay around to individuals that isn't desired to be on a website. Email has always been somewhat poor at the use case of instant messaging, but that's okay, it does other things much better than instant messaging (try finding an instant message from ten years ago and migrating it from the service it was on to a new one). Saying that it's not as good as the security models of instant messaging when being used like an instant messager is not a good reason to stop using it entirely. There are other reasons given that are more compelling, but this one seemed to so fundamentally misunderstand what some people use email for that I though it was important to note.