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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

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
      No problem, apologies for my response based on a misunderstanding. > 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. This is an intuitive idea, but I’ll also hazard that it’s probably security theater: at a “building blocks” level, a theoretical NSA that breaks Signal’s crypto has broken the finite subgroup problem that underpins all of PGP’s cryptography as well. (The reality is that the NSA doesn’t crack this kind of cryptography, at least not when it’s done correctly. They’re much bigger fans of exploits and implants, which they are absolutely not wasting on “ordinary” criminals.)

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
    No problem, apologies for my response based on a misunderstanding. > 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. This is an intuitive idea, but I’ll also hazard that it’s probably security theater: at a “building blocks” level, a theoretical NSA that breaks Signal’s crypto has broken the finite subgroup problem that underpins all of PGP’s cryptography as well. (The reality is that the NSA doesn’t crack this kind of cryptography, at least not when it’s done correctly. They’re much bigger fans of exploits and implants, which they are absolutely not wasting on “ordinary” criminals.)