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The PGP Problem

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Re: The PGP Problem

#241

Post by fipar »

toxik wrote: post #129
floatingatoll wrote: post #102

Earlier quoted context omitted.

Incorrect. Audio messages are deleted two minutes after playback by default.

Which is a receiver-side setting and can be set to one year. Your point is moot.

This is unrelated to the current discussion and not meant to contradict your "Your point is moot", but instead just as a hopefully useful anecdote: In my experience, this requires the sender to choose 'Keep' too. I have been bitten several times by me sending an audio message to my wife because I was in a situation in which typing was complicated for me (outdoors, plenty of sunshine, I don't have the best eyesight), only to find that she never even got to see it because it got self-deleted after a few minutes.

My conjecture from looking at how this has worked for me is that the sender must choose 'Keep' so that the audio message stays on the receiver's phone until listened, and the recipient must choose 'Keep' so that the audio message stays on their phone after listening.

I, of course, have no proof of this other than my own experience on devices a few years old (iphones 5 and 6).

Re: The PGP Problem

#242

Post by nickpsecurity »

mike_hearn wrote: post #228
bennofs wrote: post #176

I understand that there are better tools for encryption, but is there anything that replaces the identity management of PGP? Having a standard format for sharing identities is necessary in my opinion. If I have a friend (with whom I already exchanged keys) refer me to some third friend, it would be nice if he can just send me the identity. Sending me the signal fingerprint isn't a solution for two reasons: - I don't…

The CA system is strictly better than PGP for identity management in every respect. People often think it must be the opposite but this is essentially emotional reasoning: the Web of Trust feels decentralised, social, "webby" un"corporate", free, etc. All things that appeal to hobbyist geeks with socialist or libertarian leanings, who see encryption primarily through the activist lens of fighting governments / existi…

In an otherwise good write-up, I disagreed with this line:

" There is no scope for difference between a “big corporate” CA and a “small politically active” CA because the work they do is so mechanical, auditable and predictable."

There is room for a politically-active CA like there is for anything else. In each market, there's players that get business for doing better things for privacy, being eco-friendly, being more inclusive, etc. Things that get business from vote with your wallet types. My idea, inspired by Praxis doing Mondex's CA, was a non-profit or public-benefit company that had built into its charter and legal agreements many protections for the customers in a country without secret laws/courts like U.S. Patriot Act. The CA would also be mandated to use high-security approaches for everything it did instead of just HSM's. They might also provide services like digital notary.

In short, I can imagine more trustworthy and innovative CA's being made. I'd easily pay one like that over the rest. I'm sure there's some number of people and businesses out there that think the same way. I wouldn't try it as main business, though, since market is too cut-throat. My idea was a company like Mozilla would try it to see what happens. Let's Encrypt confirmed the non-profit, public-benefit part being feasible.

Re: The PGP Problem

#243

Post by fipar »

So, as a technical person (I can write and debug software, deploy it to production, etc.) but only an end-user when it comes to cryptography:

What are the biggest weakenesses of using PGP for local file encryption?

My use case is I have a 'vault' of secrets that I store in a gpg-encrypted org file, with a key binding in emacs to let me easily decrypt this 'vault'.

The encryption is done with gnupg's symmetric encryption, i.e., just me typing a passphrase, not using my private key. This encrypted file resides in a Filevault-encrypted drive, and is backed up to a an encrypted TimeMachine backup. It never leaves my local drive or the external USB drive I use for backups (at least not that I know of).

What are my biggest risks here? I did not get much info from the article on this use case other than "perhaps wait for age". I understand I could be using an encrypted volume that I mount on demand, which I already do for other use cases, but that would get rid of the convenience of having this "vault" available to me just one emacs shortcut away. I'm willing to give that up if the risks are big enough but I'm kindly asking the knowledgeable HN audience for advice to see what I'm doing is really that bad.

Re: The PGP Problem

#244

Post by [deleted] »

Perceptes wrote: post #211
cyphar wrote: post #22

Earlier quoted context omitted.

Is there a specific issue other than "it's not the default" that precludes it from secure messaging? This is the thing I don't understand about your position -- you have been saying for a very long time that "it's not ready yet" but as far as I can see the default-to-unencrypted setup is the main issue you have with it? I get that asking a journalist to use it right now is a bad idea, but if E2EE was the default toda…

I'd also be interested to hear Thomas clarify this. I saw a recent thread on Twitter where he and bascule were talking about it and it still wasn't super clear, but one specific point I recall is that Matrix has a significant amount of metadata stored on the server side which constructs a social graph. As opposed to something like Signal which has close to nothing stored on the server. To me this seems like an issue…

[deleted]

Re: The PGP Problem

#245

Post by dunkelheit »

tptacek wrote: post #219
dunkelheit wrote: post #197

Earlier quoted context omitted.

> > Put a Signal number on your security page to receive bug bounty reports, not a PGP key. Does anyone actually do this? Even Signal developers themselves don't! (see https://support.signal.org/hc/en-us/articles/360007320791-Ho... ). Instead there is a plain old email address where you are supposed to send your Signal number so that you can chat.

We manage bug bounties for a bunch of different startups, and I can count on zero fingers the number of times I've had to use PGP in the past year for that. In practice, people just send bugs with plain 'ol email.

So even Latacora-advised startups use plain old email for bug bounties. Why then does the blog post recommend using Signal for that?

Re: The PGP Problem

#246

Post by floatboth »

srl wrote: post #21

First, thanks enormously for writing this -- and for all the other recent articles that have appeared here the vein of "PGP is as bad as it is unpleasant to use". It's a point I didn't really appreciate (at least as much as I (sh/c)ould have) and I'm sure I'm not alone. It seems that the state of package distribution for many distributions is poor, security-wise. (OpenBSD, to nobody's surprise, is an exception.) For…

I don't know where you found MD5, most PKGBUILDs have `sha256sums` in them.

Package signing is (hot take!) overrated and can be somewhat theater. It helps if your package manager connects to third party mirrors, but otherwise, the only threat it protects against is "the https server is compromised but the package build farm is not". I don't know why anyone would worry so much about that.

Re: The PGP Problem

#247

Post by Leace »

Natanael_L wrote: post #225
Leace wrote: post #188

Earlier quoted context omitted.

> persistent global public identity Certificate Transparency could be reused/abused to host it. If, for example, you issued a cert for name .contact.example.com and the tooling would check CT logs this could be a very powerful directory of contacts. Using CT monitors you could see if/when someone tampers with your domain name contact keys. Mozilla is planning something similar for signing software: https://wiki.mozil…

This is basically the keybase.io log system. Although they too rely on PGP currently

Minus the network of independent logs as from what I remember only keybase.io runs their own log system. Although they do timestamp their Merkle tree roots into Bitcoin.

Re: The PGP Problem

#248

Post by tptacek »

dunkelheit wrote: post #245
tptacek wrote: post #219

Earlier quoted context omitted.

We manage bug bounties for a bunch of different startups, and I can count on zero fingers the number of times I've had to use PGP in the past year for that. In practice, people just send bugs with plain 'ol email.

So even Latacora-advised startups use plain old email for bug bounties. Why then does the blog post recommend using Signal for that?

Because Signal would be better than the PGP theater. In practice, though, it doesn't matter; people are just going to use plain old email no matter what. They're not going to encrypt their findings to you.

Re: The PGP Problem

#249

Post by Natanael_L »

afiori wrote: post #137
AmericanChopper wrote: post #98

Earlier quoted context omitted.

I think the real problem is that nobody has ever created a decent PKI, and I doubt a sufficiently secure PKI is even possible. CAs require you to trust people that aren’t supposed to be party to the communication (trust both not to be hostile, and not to be insecure themselves). All other forms of PKI offer entirely impractical authentication mechanisms. With signal and the like, your options are 1) Verify keys by be…

with signal I believe you can have already trusted contacts vouch for new contacts

You're thinking of PGP web of trust, Signal doesn't have that

Re: The PGP Problem

#250

Post by yitosda »

fipar wrote: post #243

So, as a technical person (I can write and debug software, deploy it to production, etc.) but only an end-user when it comes to cryptography: What are the biggest weakenesses of using PGP for local file encryption? My use case is I have a 'vault' of secrets that I store in a gpg-encrypted org file, with a key binding in emacs to let me easily decrypt this 'vault'. The encryption is done with gnupg's symmetric encrypt…

There's nothing wrong with this. Public/Private keys are for sharing secrets and proving identity.

Assuming you are using a sane cipher and mode, your risks boil down to any of a myriad of methods of stealing/bruteforcing your key or grabbing the unencrypted file.

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