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The PGP Problem

latacora.micro.blog

221–230 of 369 posts

Re: The PGP Problem

#221

There's a few places where this engages in goalpost shifting that seems less than helpful even though I end up agreeing with the general thrust. Let's focus on one: > Put a Signal number on your security page to receive bug bounty reports, not a PGP key. We can reasonably assume in 2019 that this "security page" is from an HTTPS web site, so it's reasonably safe against tampering, but a "Signal number" is just a phon…

Keybase.io supports this usecase

Re: The PGP Problem

#222
post #117

Telling people to treat email as insecure and thus not use it for anything serious is terrible bad advice. I am reminded of BGP (Border Gateway Protocol). Anyone who has even glanced at the RFC of BGP could write an essay of the horrible mess of compatibility, extensions, non-standard design of BGP. It also lack any security consideration. The problem is that it is the core infrastructure of the Internet. Defining so…

People that use email to convey sensitive messages will be putting themselves and others at risk, whether or not they use PGP, for the indefinite future. That's a simple statement of fact. I understand that you don't like that fact --- nobody does! --- but it remains true no matter how angry it makes you.

Re: The PGP Problem

#223

FYI, Robert J. Hansen's comment in gnupg-users@gnupg.org.[0] 0) https://lists.gnupg.org/pipermail/gnupg-users/2019-July/0623...

I don't understand how these represent "mistakes", let alone "serious mistakes". But I'm glad he liked it.

Re: The PGP Problem

#224
post #2

Really, all I did here was combine posts from Matthew Green, Filippo Valsorda, and George Tankersley into one post, and then talk to my partner LVH about it. So blame them. (also 'pvg, who said i should write this, and it's been nagging at me ever since)

Is it wrong to use openssl to encrypt files? 0. (Only once) generate key pair id_rsa.pub.pem, id_rsa.pem 1. Generate random key openssl rand -base64 32 > key.bin 2. Encrypt key openssl rsautl -encrypt -inkey id_rsa.pub.pem -pubin -in key.bin -out key.bin.enc 3. Encrypt file using key openssl enc -aes-256-cbc -salt -in SECRET_FILE -out SECRET_FILE.enc -pass file:./key.bin -- other side -- 4. Decrypt key openssl rsautl…

To start with, none of that encryption is authenticated.

Re: The PGP Problem

#225
post #188

There's a few places where this engages in goalpost shifting that seems less than helpful even though I end up agreeing with the general thrust. Let's focus on one: > Put a Signal number on your security page to receive bug bounty reports, not a PGP key. We can reasonably assume in 2019 that this "security page" is from an HTTPS web site, so it's reasonably safe against tampering, but a "Signal number" is just a phon…

> 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

Re: The PGP Problem

#226

Earlier quoted context omitted.

You might be surprised just how many mail providers support STARTTLS for email, at least opportunistically. https://www.fastmail.com/help/technical/ssltlsstarttls.html

And opportunistic STARTTLS is vulnerable to downgrade attacks by MITM. the problems with email are that, no matter how sure you are that the connection between you and your mail server, and your local and server storage, are secure, the parties you may be interacting with are not. And then, as is talked about in the article, your recipient forwards the mail as plaintext...

And downgrade attacks are mitigated by MTA-STS: https://www.hardenize.com/blog/mta-sts

Not supported by everyone just yet since this is a new standard, but Gmail at least supports it.

Re: The PGP Problem

#227
post #162

> there’s a simple meta-problem with it: it was designed in the 1990s, before serious modern cryptography SSL was designed in 1994 but it has been properly maintained and today no-one argues that TLS should be replaced by noise/strobe etc. OpenPGP's problem no 1. is that there are no parties using it on a wider scale and interested in improving it.

SSL 2.0 was overhauled (by cryptographic experts) to create TLS, and, after something like 10 years of effort, support for SSL 2.0 was scourged off the Internet. And still, we had the DROWN attack a couple years ago, which manages to exploit cross-protocol attacks between SSL 2.0 and TLS on different servers. In the last few years, we got TLS 1.3, which again made significant, breaking changes with the previous versions of the protocol (such as getting rid of the RSA handshake), and presumably over the next 10 years we'll be shedding support for all previous versions of TLS.

That's what didn't happen with PGP.

Re: The PGP Problem

#228

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 / existing social power structures.

But there's nothing secure about the WoT. As the post points out, the entire thing is theatre. Effectively the WoT converts every PGP user into a certificate authority, but they can't hope to even begin to match the competence of even not very competent WebTrust audited CAs. Basic things all CAs are required to do, like use hardware security modules, don't apply in the WoT, where users routinely do unsafe things like use their private key from laptops that run all kinds of random software pulled from the net, or carry their private keys through airports, or accept an email "From" header as a proof of identity.

I wrote about this a long time ago here:

https://blog.plan99.net/why-you-think-the-pki-sucks-b64cf591...

Re: The PGP Problem

#229

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…

I think that currently Keybase.io is the only thing trying to be universal, with their transparency log plus links to external profiles along with signed attestations for them.

But even that's still not quite what I'm looking for. There's no straightforward way to link arbitary protocol accounts / identities to it, outside of linking plain URL:s.

We need something a bit smarter than keybase that would actually allow you to maintain a single personal identifier across multiple protocols.

Re: The PGP Problem

#230
post #100

I use my PGP key (with a Yubikey) for two things, the pass password manager and as an SSH authentication key. Is there a replacement for those two use cases where I can store my private key on a hardware token?

I use the GPG compatibility goo to get an SSH key out of my Yubikey 5 and that's fine, it's fine, go ahead and do that.
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