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Opmsg – A GPG Alternative

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Re: Opmsg – A GPG Alternative

#2
I am not qualified to review how it implements forward security, for instance.

But this shares a lot of the problems that GPG has. It relies on existing mail standards, so it leaks metadata all over the place, and security can easily be defeated by "accidentally replying without encrypting." It's configurable -- every choice you have to make is a chance to make the wrong one. It implements RSA, which nobody should be using anymore.

Re: Opmsg – A GPG Alternative

#3
post #2

I am not qualified to review how it implements forward security, for instance. But this shares a lot of the problems that GPG has. It relies on existing mail standards, so it leaks metadata all over the place, and security can easily be defeated by "accidentally replying without encrypting." It's configurable -- every choice you have to make is a chance to make the wrong one. It implements RSA, which nobody should be…

Indeed, from Latacora's recent "The PGP Problem":

> Encrypting Email

> Don’t.

> Email is insecure. Even with PGP, it’s default-plaintext, which means that even if you do everything right, some totally reasonable person you mail, doing totally reasonable things, will invariably CC the quoted plaintext of your encrypted message to someone else (we don’t know a PGP email user who hasn’t seen this happen). PGP email is forward-insecure. Email metadata, including the subject (which is literally message content), are always plaintext.

> If you needed another reason, read the Efail paper. The GnuPG community, which mishandled the Efail disclosure, talks this research down a lot, but it was accepted at Usenix Security (one of the top academic software security venues) and at Black Hat USA (the top industry software security venue), was one of the best cryptographic attacks of the last 5 years, and is a pretty devastating indictment of the PGP ecosystem. As you’ll see from the paper, S/MIME isn’t better.

> This isn’t going to get fixed. To make actually-secure email, you’d have to tunnel another protocol over email (you’d still be conceding traffic analysis attacks). At that point, why bother pretending?

> Encrypting email is asking for a calamity. Recommending email encryption to at-risk users is malpractice. Anyone who tells you it’s secure to communicate over PGP-encrypted email is putting their weird preferences ahead of your safety.

Re: Opmsg – A GPG Alternative

#4
post #3
post #2

I am not qualified to review how it implements forward security, for instance. But this shares a lot of the problems that GPG has. It relies on existing mail standards, so it leaks metadata all over the place, and security can easily be defeated by "accidentally replying without encrypting." It's configurable -- every choice you have to make is a chance to make the wrong one. It implements RSA, which nobody should be…

Indeed, from Latacora's recent "The PGP Problem": > Encrypting Email > Don’t. > Email is insecure. Even with PGP, it’s default-plaintext, which means that even if you do everything right, some totally reasonable person you mail, doing totally reasonable things, will invariably CC the quoted plaintext of your encrypted message to someone else (we don’t know a PGP email user who hasn’t seen this happen). PGP email is f…

If you know what you're doing, PGP can improve security. The real problem is that, the moment you're sending information to someone, you're giving that information away, out of your control.

If I understand it correctly, all the above points seem to address mostly the technical aspect, that someone who means well may too easily leak previously encrypted information out of ignorance.

A possible counter argument could be this: You already need to trust a recipient that they won't leak the data you send them willingly and with harmful intent, so it's not that much to ask that people also trust the competence of the recipient.

What Opmsg really seems to be about is cases where you don't trust the recipient to not betray you, intentionally or unintentionally.

Re: Opmsg – A GPG Alternative

#6
I think a perhaps unclear part of the recent post "The PGP Problem" is that PGP is bad for email.

If you don't use it for email, I don't see it as really a problem. Unless, maybe, you are a reporter or otherwise not clear on the principles behind using something like GPG. I think personally that the point about all the discussion is that for laypeople PGP and email is just too complicated (even for myself as a programmer and evidently for others it is complicated).

In that same vein, I can see how PGP has fundamental limitations with email, e.g.: Having someone's email address does not imply that you have their public key. Is it possible to state in simple terms whether OP's program does to improve this?

Re: Opmsg – A GPG Alternative

#7
post #6

I think a perhaps unclear part of the recent post "The PGP Problem" is that PGP is bad for email . If you don't use it for email, I don't see it as really a problem. Unless, maybe, you are a reporter or otherwise not clear on the principles behind using something like GPG. I think personally that the point about all the discussion is that for laypeople PGP and email is just too complicated (even for myself as a progr…

Exactly. The "PGP is bad because public key infrastructure management is hard" meme should please die already.

The idea of a dedicated package signing and encrypting tool detached from this problem is maybe not a bad idea in that regard, because it removes this stigma.

Re: Opmsg – A GPG Alternative

#8
post #6

I think a perhaps unclear part of the recent post "The PGP Problem" is that PGP is bad for email . If you don't use it for email, I don't see it as really a problem. Unless, maybe, you are a reporter or otherwise not clear on the principles behind using something like GPG. I think personally that the point about all the discussion is that for laypeople PGP and email is just too complicated (even for myself as a progr…

> I think a perhaps unclear part of the recent post "The PGP Problem" is that PGP is bad for email. If you don't use it for email, I don't see it as really a problem.

You're apparently asserting that Latacora's "The PGP Problem" states PGP is only bad for email. I can only assume you didn't even bother the article? Because it states that PGP is bad:

* period and in its entirety, in fact most of the article (section 1 "The Problems") is the various ways PGP and GnuPG are broken at the core, specific scenarios are only mentioned (in section 2 "The Answers") to provide alternatives, because Latacora's assertion is that in cryptography one size does not fit all, and each scenario needs its own toolset

* for securing messenging

* for securing email messages

* for signing files and packages

* for encrypting files, whether to send, backups, application data, …

What it does state with respect to email is that encrypting emails is a fool's errand not just that using PGP to do so is a mistake. It does note that GnuPG is also specifically bad at it, but very clearly state the issue is not limited to PGP:

> This isn’t going to get fixed. To make actually-secure email, you’d have to tunnel another protocol over email (you’d still be conceding traffic analysis attacks). At that point, why bother pretending?

> Encrypting email is asking for a calamity. Recommending email encryption to at-risk users is malpractice.

Re: Opmsg – A GPG Alternative

#9
post #6

I think a perhaps unclear part of the recent post "The PGP Problem" is that PGP is bad for email . If you don't use it for email, I don't see it as really a problem. Unless, maybe, you are a reporter or otherwise not clear on the principles behind using something like GPG. I think personally that the point about all the discussion is that for laypeople PGP and email is just too complicated (even for myself as a progr…

My understanding is quite different. Email is inherently insecure and there is nothing you can do about it.

PGP is insecure for everything else as well

The Latacora article was eye-opening for me on the email problem - quite simply if I send an encrypted mail to a friend / collegue - which I intend them to read, and they read it and quote it to someone else in plain text then that's it - my plaintext and my cipher are available in the wild and my key (my long term key) is effectively broken.

I simply never thought it through that way. But that's how email is supposed to be used - it will be used that way.

Mind Blown.

Re: Opmsg – A GPG Alternative

#10
The reality of the situation is that you can't remove the human factor from security. So someone copying your email to someone else is a human problem that can't be fixed - someone could just as easily photograph the screen.

The reality is email will continue to be used, and there is a use case for being able to send an email securely to another person.

EFail was pretty bad, but only affected HTML email.

Having a modicum of backwards compatibility is how to encourage transitioning to new tech, so the RSA implementation makes sense.

I must say this is the first decent alternative I've seen for GPG instead of rants about Signal and specialised tooling that just ignore the issue that folks want to be able to send secure emails to each other.

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