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PGP over email is used in the real world and used successfully. Research about online black markets (which serves as a nice "case study") will show that the ma

PGP over email is used in the real world and used successfully. Research about online black markets (which serves as a nice "case study") will show that the main form of communication between people there have been pasting a PGP encrypted message into a text box and sending it, and sometimes literally using email. In a situation like this, where anonymity and privacy are critical, signal is not even remotely an option because it requires a phone number. Matrix may be possible to use, but it would require that someone run a matrix server that allow people to make accounts with no information required for sign up, and allow signup and use of the server over tor, which are all unlikely. PGP over email or pasted into a web form is simple, it doesn't require signing up with a phone number or any PI, it can be used over tor, and it can be done with basic utils installed on almost any Linux distro. I suspect a lot of cryptographers have not done research about what goes on "in the real world" or "in the wild". It would be interesting for them to setup a mock situation where two people attempt to send messages to each other without doing anything that could identify them in any way, completely anonymously, to emulate what using these tools in the real world would be like for a whistleblower or journalist or whatever.

woodruffw 3y ago
It's worth reading through the criminal complaints against various Silk Road people[1]. You'll notice two things: (1) the government nails these people despite encrypted messages, because their email metadata is more than sufficient, and (2) people whose literal lives depend on using PGP correctly fail to do so (e.g. by sending some messages without encryption, or forwarding previously encrypted messages as unencrypted). PGP is not a serious answer here. [1]: https://www.justice.gov/sites/default/files/opa/press-releases/attachments/2015/03/30/criminal_complaint_forcev2.pdf https://www.justice.gov/sites/default/files/opa/press-releas...
- chlorion 3y ago
  I agree that it's error prone and far from ideal, and that most people should be using signal or matrix or something, but I'm not sure what other practical answers there are for more intense cases where people don't have access to those things.
  - woodruffw 3y ago
    That's the thing: Signal and Matrix are still the right answer for those cases! Consider the ANOM[1] case: the FBI found it easier to FUD criminals into using a backdoored chat app than to break actual chat apps. [1]: https://slate.com/technology/2021/12/fbi-fake-encrypted-messaging-platform-anom-sky-global.html https://slate.com/technology/2021/12/fbi-fake-encrypted-mess...
- 0xDEAFBEAD 3y ago
  There's a selection effect here -- the criminal complaints are the people who got caught. And drug dealers aren't exactly known for technical literacy. I think the usability complaints here are very valid, but chlorion has a good point that PGP still wins for particular use cases. Heck, if you're really paranoid [and metadata is not your primary concern], use PGP over Signal. I don't think any of the alternatives proposed in this thread are chainable in this way like PGP.
  - woodruffw 3y ago
    There's a problem here: we can't make falsifiable claims about the criminals who aren't caught. I could just as easily say the same thing about Signal! There's one critical difference, however: governments have identified Signal and its ilk specifically as a threat to their intelligence gathering capabilities. They don't talk this way about PGP; the public signals overwhelmingly indicate that (1) virtually nobody uses PGP for anything worth surveilling, and (2) anybody who does use it for things worth surveilling bungles it (see above). Thats the government's dream! > Heck, if you're really paranoid [and metadata is not your primary concern], use PGP over Signal. I don't think any of the alternatives proposed in this thread are chainable in this way like PGP. This doesn't make sense. What is the "paranoid" model in which PGP provides (1) better cryptographic guarantees and (2) metadata isn't your primary concern? PGP cannot provide forward secrecy, provides all-around weaker cryptographic primitives, and is significantly harder to use correctly. It isn't a rational choice for a paranoid actor to make.
    - 0xDEAFBEAD 3y ago
      >This doesn't make sense. What is the "paranoid" model in which PGP provides (1) better cryptographic guarantees and (2) metadata isn't your primary concern? PGP cannot provide forward secrecy, provides all-around weaker cryptographic primitives, and is significantly harder to use correctly. It isn't a rational choice for a paranoid actor to make. I think you must have misunderstood me. By "PGP over Signal" I meant PGP-encrypting messages and pasting the ASCII-armored ciphertext into the Signal client. The idea being that even if the NSA can break Signal's crypto, they might fail to also break whatever crypto you select with PGP. I should have said "both PGP and Signal", sorry for the poor communication. I acknowledge PGP's flaws, but I like it as a ubiquitous DIY tool. I'm hoping that niche gets filled with something better. Though to be honest, I think for the "ubiquitous DIY tool" niche, forward secrecy might just be impractical.

woodruffw 3y ago

It's worth reading through the criminal complaints against various Silk Road people[1]. You'll notice two things: (1) the government nails these people despite encrypted messages, because their email metadata is more than sufficient, and (2) people whose literal lives depend on using PGP correctly fail to do so (e.g. by sending some messages without encryption, or forwarding previously encrypted messages as unencrypted). PGP is not a serious answer here. [1]: https://www.justice.gov/sites/default/files/opa/press-releases/attachments/2015/03/30/criminal_complaint_forcev2.pdf https://www.justice.gov/sites/default/files/opa/press-releas...

chlorion 3y ago
I agree that it's error prone and far from ideal, and that most people should be using signal or matrix or something, but I'm not sure what other practical answers there are for more intense cases where people don't have access to those things.
- woodruffw 3y ago
  That's the thing: Signal and Matrix are still the right answer for those cases! Consider the ANOM[1] case: the FBI found it easier to FUD criminals into using a backdoored chat app than to break actual chat apps. [1]: https://slate.com/technology/2021/12/fbi-fake-encrypted-messaging-platform-anom-sky-global.html https://slate.com/technology/2021/12/fbi-fake-encrypted-mess...
0xDEAFBEAD 3y ago
There's a selection effect here -- the criminal complaints are the people who got caught. And drug dealers aren't exactly known for technical literacy. I think the usability complaints here are very valid, but chlorion has a good point that PGP still wins for particular use cases. Heck, if you're really paranoid [and metadata is not your primary concern], use PGP over Signal. I don't think any of the alternatives proposed in this thread are chainable in this way like PGP.
- woodruffw 3y ago
  There's a problem here: we can't make falsifiable claims about the criminals who aren't caught. I could just as easily say the same thing about Signal! There's one critical difference, however: governments have identified Signal and its ilk specifically as a threat to their intelligence gathering capabilities. They don't talk this way about PGP; the public signals overwhelmingly indicate that (1) virtually nobody uses PGP for anything worth surveilling, and (2) anybody who does use it for things worth surveilling bungles it (see above). Thats the government's dream! > Heck, if you're really paranoid [and metadata is not your primary concern], use PGP over Signal. I don't think any of the alternatives proposed in this thread are chainable in this way like PGP. This doesn't make sense. What is the "paranoid" model in which PGP provides (1) better cryptographic guarantees and (2) metadata isn't your primary concern? PGP cannot provide forward secrecy, provides all-around weaker cryptographic primitives, and is significantly harder to use correctly. It isn't a rational choice for a paranoid actor to make.
  - 0xDEAFBEAD 3y ago
    >This doesn't make sense. What is the "paranoid" model in which PGP provides (1) better cryptographic guarantees and (2) metadata isn't your primary concern? PGP cannot provide forward secrecy, provides all-around weaker cryptographic primitives, and is significantly harder to use correctly. It isn't a rational choice for a paranoid actor to make. I think you must have misunderstood me. By "PGP over Signal" I meant PGP-encrypting messages and pasting the ASCII-armored ciphertext into the Signal client. The idea being that even if the NSA can break Signal's crypto, they might fail to also break whatever crypto you select with PGP. I should have said "both PGP and Signal", sorry for the poor communication. I acknowledge PGP's flaws, but I like it as a ubiquitous DIY tool. I'm hoping that niche gets filled with something better. Though to be honest, I think for the "ubiquitous DIY tool" niche, forward secrecy might just be impractical.