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I think a perhaps unclear part of the recent post "The PGP Problem" is that PGP is bad for email. If you don't use it for email, I don't see it as really a pro

I think a perhaps unclear part of the recent post "The PGP Problem" is that PGP is bad for email. If you don't use it for email, I don't see it as really a problem. Unless, maybe, you are a reporter or otherwise not clear on the principles behind using something like GPG. I think personally that the point about all the discussion is that for laypeople PGP and email is just too complicated (even for myself as a programmer and evidently for others it is complicated). In that same vein, I can see how PGP has fundamental limitations with email, e.g.: Having someone's email address does not imply that you have their public key. Is it possible to state in simple terms whether OP's program does to improve this?

_pmf_ 7y ago
Exactly. The "PGP is bad because public key infrastructure management is hard" meme should please die already. The idea of a dedicated package signing and encrypting tool detached from this problem is maybe not a bad idea in that regard, because it removes this stigma.
masklinn 7y ago
> I think a perhaps unclear part of the recent post "The PGP Problem" is that PGP is bad for email. If you don't use it for email, I don't see it as really a problem. You're apparently asserting that Latacora's "The PGP Problem" states PGP is only bad for email. I can only assume you didn't even bother the article? Because it states that PGP is bad: * period and in its entirety, in fact most of the article (section 1 "The Problems") is the various ways PGP and GnuPG are broken at the core, specific scenarios are only mentioned (in section 2 "The Answers") to provide alternatives, because Latacora's assertion is that in cryptography one size does not fit all, and each scenario needs its own toolset * for securing messenging * for securing email messages * for signing files and packages * for encrypting files, whether to send, backups, application data, … What it does state with respect to email is that encrypting emails is a fool's errand not just that using PGP to do so is a mistake. It does note that GnuPG is also specifically bad at it, but very clearly state the issue is not limited to PGP: > This isn’t going to get fixed. To make actually-secure email, you’d have to tunnel another protocol over email (you’d still be conceding traffic analysis attacks). At that point, why bother pretending? > Encrypting email is asking for a calamity. Recommending email encryption to at-risk users is malpractice.
- bscphil 7y ago
  So what's the alternative, for asymmetrically encrypting arbitrary binary data? For sending such data to others, the Latacora article suggest a tool that I've never heard of or heard recommended by other experts called "Magic Wormhole". It's a new tool that (from what I call tell) has a whole crapload of limitations and assumptions that PGP does not have: https://magic-wormhole.readthedocs.io/en/latest/welcome.html#design https://magic-wormhole.readthedocs.io/en/latest/welcome.html... One of the most severe is that it apparently requires both ends to have active internet connections to transfer the data over the wire between them. As I type this, I'm visiting my parents who have 5 Mbps internet. Let's hope that file isn't big or my contact has the time and patience to wait if it is! The other is that it apparently relies on a shared password, which just takes us back to encryption before the very problem PGP was designed to solve... For simply "encrypting files", even Latacora gives up and says "use PGP"!! As a side note, though I agree with them that PGP is not good for secure messaging, I don't find their alternatives convincing there either. Signal and Wire don't have solid group chat capabilities that don't rely on a single central server run by a third party and don't require private information like a phone number to use. I consider that absolutely basic for a good messenger. At least PGP, though very faulty in this area, is designed to be used over existing protocols like email to make them secure, so it doesn't have the last two limitations.
  - tptacek 7y ago
    Wormhole isn't new, and if you haven't heard another "expert" recommend it, you don't hang out with a lot of cryptography engineers. The point about "simply encrypting files" is that nobody is implementing something with PGP's "encrypt-a-file" interface because it's not that useful; rather, people purposefully design modern systems with cryptography tailored to tasks, like messaging or file transfer or backup. Your last point about PGP vs. Signal is pretty funny, as it implies that PGP has "solid group chat capabilities".
    - bscphil 7y ago
      > Wormhole isn't new, and if you haven't heard another "expert" recommend it, you don't hang out with a lot of cryptography engineers. You're right, I don't. But the earliest thing I found about Wormhole after a quick look was from 2015, which I think is pretty recent in the crypto world. Maybe I missed something. > Your last point about PGP vs. Signal is pretty funny, as it implies that PGP has "solid group chat capabilities". I tried to be clear about the fact that I wasn't saying that. Its benefits over Signal and Wire (but not Matrix) are that it doesn't require a central server and doesn't require any PII to sign up. I consider those crucial for anyone who has extreme security / privacy needs. PGP completely sucks for group messaging, I agree. But the alternatives suggested are simply non-starters for many use cases.
lifeisstillgood 7y ago
My understanding is quite different. Email is inherently insecure and there is nothing you can do about it. PGP is insecure for everything else as well The Latacora article was eye-opening for me on the email problem - quite simply if I send an encrypted mail to a friend / collegue - which I intend them to read, and they read it and quote it to someone else in plain text then that's it - my plaintext and my cipher are available in the wild and my key (my long term key) is effectively broken. I simply never thought it through that way. But that's how email is supposed to be used - it will be used that way. Mind Blown.
- mkesper 7y ago
  Messages are encrypted with a session key in openpgp so this doesn't work.
  - lifeisstillgood 7y ago
    How do I negotiate a session key with the email recipient? it's a single transmission? otherwise it's a one time pad perhaps - but then that defeats the point of the public key ? would you mind expanding on this as it is an interesting area
    - blattimwind 7y ago
      A random key is used to encrypt the email, then that random key is asymmetrically encrypted using the recipient's public RSA key. You do not use your own key to encrypt mails to someone else. Indeed, you can send encrypted emails without even having a key of your own.
      - lifeisstillgood 7y ago
        So I actually re-read and followed links (I mean whats wrong with lazy assumptions anymore) tptacek's "why email is insecure" post is here: https://news.ycombinator.com/item?id=16088386 https://news.ycombinator.com/item?id=16088386 And yes thats what he says in the original latacora post. I read the article '''invariably CC the quoted plaintext of your encrypted message to someone else (we don’t know a PGP email user who hasn’t seen this happen)''' So I made the (incorrect) leap to pgp using the long term key to encrypt files. My bad. But this does not fix the original point it seems - email is not going to be "secure" any time soon. But you can send encrypted files over email to people.

_pmf_ 7y ago

Exactly. The "PGP is bad because public key infrastructure management is hard" meme should please die already. The idea of a dedicated package signing and encrypting tool detached from this problem is maybe not a bad idea in that regard, because it removes this stigma.

masklinn 7y ago

> I think a perhaps unclear part of the recent post "The PGP Problem" is that PGP is bad for email. If you don't use it for email, I don't see it as really a problem. You're apparently asserting that Latacora's "The PGP Problem" states PGP is only bad for email. I can only assume you didn't even bother the article? Because it states that PGP is bad: * period and in its entirety, in fact most of the article (section 1 "The Problems") is the various ways PGP and GnuPG are broken at the core, specific scenarios are only mentioned (in section 2 "The Answers") to provide alternatives, because Latacora's assertion is that in cryptography one size does not fit all, and each scenario needs its own toolset * for securing messenging * for securing email messages * for signing files and packages * for encrypting files, whether to send, backups, application data, … What it does state with respect to email is that encrypting emails is a fool's errand not just that using PGP to do so is a mistake. It does note that GnuPG is also specifically bad at it, but very clearly state the issue is not limited to PGP: > This isn’t going to get fixed. To make actually-secure email, you’d have to tunnel another protocol over email (you’d still be conceding traffic analysis attacks). At that point, why bother pretending? > Encrypting email is asking for a calamity. Recommending email encryption to at-risk users is malpractice.

bscphil 7y ago
So what's the alternative, for asymmetrically encrypting arbitrary binary data? For sending such data to others, the Latacora article suggest a tool that I've never heard of or heard recommended by other experts called "Magic Wormhole". It's a new tool that (from what I call tell) has a whole crapload of limitations and assumptions that PGP does not have: https://magic-wormhole.readthedocs.io/en/latest/welcome.html#design https://magic-wormhole.readthedocs.io/en/latest/welcome.html... One of the most severe is that it apparently requires both ends to have active internet connections to transfer the data over the wire between them. As I type this, I'm visiting my parents who have 5 Mbps internet. Let's hope that file isn't big or my contact has the time and patience to wait if it is! The other is that it apparently relies on a shared password, which just takes us back to encryption before the very problem PGP was designed to solve... For simply "encrypting files", even Latacora gives up and says "use PGP"!! As a side note, though I agree with them that PGP is not good for secure messaging, I don't find their alternatives convincing there either. Signal and Wire don't have solid group chat capabilities that don't rely on a single central server run by a third party and don't require private information like a phone number to use. I consider that absolutely basic for a good messenger. At least PGP, though very faulty in this area, is designed to be used over existing protocols like email to make them secure, so it doesn't have the last two limitations.
- tptacek 7y ago
  Wormhole isn't new, and if you haven't heard another "expert" recommend it, you don't hang out with a lot of cryptography engineers. The point about "simply encrypting files" is that nobody is implementing something with PGP's "encrypt-a-file" interface because it's not that useful; rather, people purposefully design modern systems with cryptography tailored to tasks, like messaging or file transfer or backup. Your last point about PGP vs. Signal is pretty funny, as it implies that PGP has "solid group chat capabilities".
  - bscphil 7y ago
    > Wormhole isn't new, and if you haven't heard another "expert" recommend it, you don't hang out with a lot of cryptography engineers. You're right, I don't. But the earliest thing I found about Wormhole after a quick look was from 2015, which I think is pretty recent in the crypto world. Maybe I missed something. > Your last point about PGP vs. Signal is pretty funny, as it implies that PGP has "solid group chat capabilities". I tried to be clear about the fact that I wasn't saying that. Its benefits over Signal and Wire (but not Matrix) are that it doesn't require a central server and doesn't require any PII to sign up. I consider those crucial for anyone who has extreme security / privacy needs. PGP completely sucks for group messaging, I agree. But the alternatives suggested are simply non-starters for many use cases.

lifeisstillgood 7y ago

My understanding is quite different. Email is inherently insecure and there is nothing you can do about it. PGP is insecure for everything else as well The Latacora article was eye-opening for me on the email problem - quite simply if I send an encrypted mail to a friend / collegue - which I intend them to read, and they read it and quote it to someone else in plain text then that's it - my plaintext and my cipher are available in the wild and my key (my long term key) is effectively broken. I simply never thought it through that way. But that's how email is supposed to be used - it will be used that way. Mind Blown.

mkesper 7y ago
Messages are encrypted with a session key in openpgp so this doesn't work.
- lifeisstillgood 7y ago
  How do I negotiate a session key with the email recipient? it's a single transmission? otherwise it's a one time pad perhaps - but then that defeats the point of the public key ? would you mind expanding on this as it is an interesting area
  - blattimwind 7y ago
    A random key is used to encrypt the email, then that random key is asymmetrically encrypted using the recipient's public RSA key. You do not use your own key to encrypt mails to someone else. Indeed, you can send encrypted emails without even having a key of your own.
    - lifeisstillgood 7y ago
      So I actually re-read and followed links (I mean whats wrong with lazy assumptions anymore) tptacek's "why email is insecure" post is here: https://news.ycombinator.com/item?id=16088386 https://news.ycombinator.com/item?id=16088386 And yes thats what he says in the original latacora post. I read the article '''invariably CC the quoted plaintext of your encrypted message to someone else (we don’t know a PGP email user who hasn’t seen this happen)''' So I made the (incorrect) leap to pgp using the long term key to encrypt files. My bad. But this does not fix the original point it seems - email is not going to be "secure" any time soon. But you can send encrypted files over email to people.