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The PGP Problem

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Re: The PGP Problem

#111

Post by fanf2 »

terom wrote: post #80

> Encrypting Files > This really is a problem. If you’re/not/ [...] then there’s no one good tool that does this now. Filippo Valsorda is working on “age” for these use cases, and I’m super optimistic about it, but it’s not there yet. I've been (ab)using ansible-vault for this. It's apparently[1] now using reasonable primitives (PBKDF2+AES-CTR+HMAC-SHA256), but not necessarily the latest and bestest ones: https://git…

I have some notes on why I (and some of my colleagues) use gpg instead of Ansible vault: https://dotat.at/prog/regpg/doc/rationale.html

I would dearly like a replacement for gpg in this context; `age` by Filippo Valsorda and Ben Cartwright-Cox looks like it will be nice, though I would like it to be easier to audit the recipients of encrypted files. Note that this kind of auditing relies on an information leak that cryptographers usually try to suppress...

Re: The PGP Problem

#112

Post by acqq »

PGP has issues, but for many use scenarios there is effectively no ready alternative at the moment.

Until there is, whoever already uses or knows how to use GPG is still better off using GPG than not using anything.

Signal is especially not a good replacement for anybody who doesn't want to have "secure" communication connected to his (or any) phone number and to the central server.

The major issue with GPG is that in some (many?) cases a user could believe to be more protected by using it than the user is. But the same can be said for other technologies.

And the article rightly notes that the GPG defaults are often bad.

The right question to ask first is always:

https://www.usenix.org/system/files/1401_08-12_mickens.pdf

Are you "dealing with Mossad or not-Mossad"? (Also worth noting is that somehow Edward Snowden managed to "deal with" NSA and still remain out of prison. At least he knew from the start the answer to the question.)

Still, anybody who wants to replace PGP in some PGP use-case should provide a really good alternative for that use-case.

As of right now, there isn't any better for even such a simple need as encrypting a file. Let's discuss it once we have that one, at least. And even then, we'll need to be able to open our old files, meaning we'll still need GPG for that.

Re: The PGP Problem

#113

Post by swalladge »

upofadown wrote: post #107

So the suggested solution for more secure email is just to give up on the concept of email entirely? Anything that does not do perfect forward secrecy is just pointless so there is no point in trying to keep significant discussions to refer to later. We are expected to return to a sort of virtual pre-writing stage. This is not really helpful. For all its shortcomings, PGP is pretty much all we have. If used in a stra…

I know right - they are all recommending Signal, Wire, WhatsApp, etc., but these aren't alternatives. They are all centralized, controlled by a single entity even if the underlying protocols are open. And you're right, they are instant messaging - ie. alternatives to Messenger, Hangouts, etc.

We need a modern email replacement that is decentralized, federated, et al. Something that keeps all the modern cryptographers happy, while facilitating the same kind of long form conversations and federated self-hostability that email provides.

I think Matrix is getting there, but even that is still focused on instant messaging.

Re: The PGP Problem

#114

Post by helper »

Godel_unicode wrote: post #67
jcranmer wrote: post #49

Earlier quoted context omitted.

In modern practice, email is sent over TLS sockets already. Any good email client should prohibit you from using SMTP, POP, or IMAP with TLS, and for the past few years, even the MX-MX transfers in the backend have started to become protected (albeit mostly opportunistically at this point, I believe) with TLS. So the only people who can read email are you, your counterparty, your ESP, and your counterparty's ESP, ass…

This is an excellent explanation overall, I do however think that it's important to note that opportunistic STARTTLS is vulnerable to downgrade attacks by mitm. Since this would have to be a mitm of e.g. Gmail it's not trivial by any means, but neither is it completely out of reach (see for example the periodic rerouting of the internet caused by odd BGP advertisements). One further note is that you can know post-hoc…

MTA-STS prevents downgrade attacks.

Re: The PGP Problem

#116

Post by pgeorgi »

elagost wrote: post #9

With the rapid churn of various chat clients it's hard to get something to stick, and I attempted to settle on XMPP+OMEMO (or OTR), since it's a protocol, not an "app" (eww). Not a single person I know still uses XMPP, and it's easier to just tell people "Download Signal". However, that requires a phone number, and is useless on a desktop if your phone's off. Despite being Free Software, it's fairly locked down. Secu…

I'm running a "beta test" of sorts of XMPP+OMEMA with non-technical people in my circles, and while Conversations (Android) and Monal (iOS) are getting there, there are still functionality and compatibility gaps.

Gajim is a usable client for desktops, but it's certainly picky about which users it is friendly with (that is, I can't recommend it to non-technical folks).

On the other hand "it uses IDs like email" is a concept my friends could understand, and the promise of end-to-end encryption over a server I control (as compared to some faceless organization somewhere else) was appealing to them.

And so I'm first level support for my peers and report issues upstream in the hope of improving the ecosystem.

And while it's closer to an email replacement (in that it avoids the ID issues of the WhatsApp clones and provides multiple clients for different purposes), it's still only a complement to email due to the ephemeral nature of messages, not a replacement.

Re: The PGP Problem

#117

Post by belorn »

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 something as insecure with the implied statement that we should treat it as insecure is unhelpful advice in regard to critical infrastructure. People are going to use it, continue to use it for the unforeseeable future, and continue to treat it as secure. Imperfect security tools will be applied on top, imperfectly, but it will see continued used as long as it is the best tools we have in the circumstances. Email and BGP and a lot of other core infrastructure that is hopelessly insecure will continue to be used with the assumption that they can be made to be secure, until an actually replacement is made and people start to transition over (like how ipv6 is replacing ipv4 and we are going to deprecate ipv4 if you take a very long term view of it).

Re: The PGP Problem

#118

Post by comex »

riquito wrote: post #110
garmaine wrote: post #96

Earlier quoted context omitted.

Really? When gmail came out they were explicitly up front about using the content of the email to deliver targeted ads. Has that changed?

There are a lot of misinformations around, and the Google haters crowd has plenty of pitchforks. https://safety.google/privacy/ads-and-data/ > Google does not use keywords or messages in your inbox to show you ads. Nobody reads your email in order to show you ads.

It's not misinformation. Gmail only stopped scanning messages for ad targeting in 2017:

https://www.nytimes.com/2017/06/23/technology/gmail-ads.html

Re: The PGP Problem

#119

Post by mongol »

maufl wrote: 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?

Given that you have set this up, and that both of these usecases are for your own use only, I wonder if there is any reason to change. Most criticism in the article is about the complexity on a larger scale.

Re: The PGP Problem

#120

Post by fouc »

jeroenhd wrote: post #82

Whent talking about alternatives, Signal and WhatsApp get mentioned because they're easy to use. They are. Signal is pretty secure. WhatsApp probably is as well but we can't be sure. That is, until it isn't anymore. WhatsApp already has a key extraction protocol built right in for its Web interface. Signal has a web (Electron) interface as well, and a shitty one at that, where the messages also get decrypted. For Wha…

I'm a little confused as to why you mention Signal and WhatsApp but not Telegram?
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