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.
> 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.
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.
No. Secure Messengers are designed to be hard to use unsafely. Nobody accidentally sends plaintext to a counterpart with Signal, because there's no feature in Signal that does that.
If you can't trust the recipient, there's nothing you can do. The point isn't to protect yourself from an untrustworthy recipient, it's to protect yourself from inadvertent disclosure.
You can still send text messages (including to Signal contacts by long-pressing the send button). Obviously it is harder than just sending an encrypted message.
Email is really difficult-to-impossible to secure correctly.
Take metadata. Because of how email works, it's effectively impossible to hide the To, From, and Date (or more accurately, the Received) headers. If you're worried about three-letter agencies, that's the only metadata they need, so you're screwed before you started. Theoretically, S/MIME allows you to encrypt additional headers (including the venerable Subject header), and has done so for 15 years, but I'm unaware of any email client that actually supports this feature, and the downgrade mode is pretty UX-hostile.
Another very challenging problem is that the flow of email pretty much destroys any chance of using a good secure cryptosystem. The email sender is not necessarily able to establish a direct, synchronous contact with the email recipient, even on a server basis. That makes protocol negotiation and perfect forward secrecy difficult. Not to mention that users generally expect to be able to open up email clients on unknown machines (especially webmail clients), which means practical key distribution tends to amount to "give your provider your keys," at which point the security advantage over the current state of all-connections-are-wrapped-in-TLS is negligible.
There's also the point that email's main advantage as a messaging system is its universality. But any new protocol is going to suffer from being supported in a small section of clients at first. If you can't get major email clients on board--and that includes webmail clients--then the universality of email is no longer an advantage in your proposed protocol. And if you're going to have to use a different client already, why bother with doing all the crap you have to deal with email syntax, MIME, SMTP, and IMAP?
About the only use case I can reasonably see for encrypting emails is in workflows like Bugzilla's "secure email" feature: the system is already relying on email for communication, there is a clear way to handle the recipient's key and protocol negotiation, and the metadata is irrelevant to secure.
Doesn’t To and From metadata leak on encrypted-message apps, too? WhatsApp, Telegram and Signal use mobile phone numbers as identifiers. In many countries now, you cannot buy a SIM card unless you show the vendor proof of identity, a copy of which is then provided to the state for its records. Therefore, any state actor that can put pressure on those encrypted-messaging services can reveal which phone numbers are talking to who, and therefore who is talking to who. Sure, the message text might still be secure if the end-to-end encryption works, but the metadata is vulnerable.
This is a feature, not a bug. Nobody actually wants to rely on a single entity (for or non-profit) for their communication. Nobody wants to be stuck in crappy Electron and mobile clients.
I had some hope that Matrix may be able to alleviate those concerns and provide a modern, federated chat solutions. Unfortunately their quality of implementation seems to be rather low with slow, laggy and resource-hungry clients and ridiculously resource-hungry servers and their current setup still apparently include a single "identity server".
> This is a feature, not a bug. Nobody actually wants to rely on a single entity (for or non-profit) for their communication. Nobody wants to be stuck in crappy Electron and mobile clients.
And nobody facing a nation state adversary wants to give their chat client their phone number. I really couldn't agree with you more on the nature of the problem and the status of the available solutions. It's really unfortunate that Matrix is as unfinished as it is. At least cross signing [1] is nearly done, which should eliminate the major issue making it unusable for anyone who's not technically competent and very dedicated.
I think that one of the really bad problems with gpg and openssl is that for a long time there was effectively only one implementation.
So the key thing for matrix is to create a healthy ecosystem that has multiple implementations of the protocol and make sure that the protocol can actually evolve.
Note that the 'identity server' is an optional component. As long as you stick to matrix native user IDs, there is no need to use one.
No, mostly because the Matrix homeserver still needs ridiculous amounts of memory. Apparently 1GB if you want to join one of the more crowded channels – what for could a chat server actually use 1GB of memory?! That's a billion characters you can store in there, even at hundreds of messages per second (which I suppose would make the channel unusable anyways?) you don't get to a billion characters very quickly.
'People' is a poorly defined notion here, and cannot be really used for any sane conclusions. Users have different practical, and security needs, therefore different priorities which define their behavior. PGP (and its alternatives) is to Whatsapp (and its alternatives) as apples to oranges.
My interpretation is that even if the people who are technically savvy in that specific area, if they have times they won't deal with encrypted information, how often are non-technical people going to want to deal with it?
I would say the implication is that PGP is useless for general secure communications purposes. You can be secure with it when you have very specific needs and have knowledgeable contacts, but it doesn't solve the need for communications privacy that most people have.
It's not a problem to be blamed on PGP though. A solution to shield an Average Joe's private life from his internet provider's snooping will always have its own deficiencies, exactly because of its generality.
>It implements RSA, which nobody should be using anymore
Can someone elaborate a bit? My impression was that RSA is fine with long keys, elliptic curves mainly provide shorter keys, and no decent quantum resistant algorithm emerged?
There's nothing cryptographically broken about RSA as a cryptosystem per se, but implementing it correctly is difficult. There have been multiple revisions to the standards for RSA over the years in response to various attacks. The current standard is PKCS#1 v2.2 (https://tools.ietf.org/html/rfc8017) and we should use RSAES-OAEP / RSASSA-PSS as primitives.
However a PKCS#1 1.5 compatibility mode with fixes for Bleichenbacher's oracle is also present in this standard and also specified in TLS 1.2 for compatibility reasons. In order not to provide an oracle, padding and other properties must be verified and a random premaster secret returned on failure instead of an error message, see: https://tools.ietf.org/html/rfc5246#section-7.4.7.1 . Note that under the other techniques, there are a lot of caveats and remarks.
Keys must also be carefully generated, as demonstrated by ROCA. In this case a specific format of primes was used to make prime number generation faster, which unfortunately also happens to be vulnerable to attack by Coppersmith's method. Any such key is weak in the sense that the private key can be recovered.
This is a quick overview. There's a lot of literature on attacks on RSA, particular parameter choice etc. So one argument against its use is the many issues that exist and the fact that even for experts, implementing it correctly is not easy.
The other point is that, compared to Elliptic Curve cryptosystems, RSA is (usually) more expensive as an operation and key generation is certainly more expensive. As a result, elliptic curves work better in constrained environments like on smartcards. If you want to do forward secrecy by periodically generating and throwing away random keys, elliptic curves can do this more efficiently - RSA by contrast would be slow.
RSA is hard to implement and requires a lot of key material to change hand.
On the flipside, a Ed25519 or Ed448 key can be reasonably dictated over phone (though you might need three minutes) and put into small low-res QR codes.
Additionally, Ed25519/448 are dead simple to implement; following the reference from the RFC documentation, you can implement a safe cryptographic method (encrypt/decrypt/sign/verify). You actually have to go out of your way and do things the standard doesn't include to make it unsafe.
Compare with RSA, where such a naive implementation will make you suffer through atleast 30 CVEs of the "padding oracle" or "leak private key" type.
While RSA is fine from a mathematical standpoint, Ed25519/448 are much simpler to implement with much less code and are designed to be reasonably safe. They provide the same security as a ~3500 bit (or about 4500 bit for 448) RSA key, so it's on the safe side of things.
There is no Post-QC algorithm yet, atleast none that made it through the NIST competition, some of them do involve using RSA with absurd key sizes and they'll likely fail the competition.
I don't understand the argument of dictating a key over the phone. If you care about that use case, you can just a well dictate the hash of an RSA public key.
Nobody knowns of the NIST curves have backdoors. Nobody know s if Dan Bernstein's curve has issues.
The advantage of RSA, is that we actually know how it works. I continue to be amazed that so many people advocate curves that we don't undertstand.
Of course, the big problem with RSA, is that is seems simple enough that people try to implement it themselves and get it wrong. With EC, you basically have to use one of the standard libraries.
>Nobody knowns of the NIST curves have backdoors. Nobody know s if Dan Bernstein's curve has issues.
There are still some differences. NIST provides some curves and doesn't explain much about them. You can read up how DJB choose the curves. It's a very neat and tidy process that is easy to follow and very reasonable.
ECurve isn't terribly more complicated than RSA, they both rely on multiplication, though EC does it in 2D space and RSA in Modulo space. I have implemented EC myself, the underlying math isn't that much more complicated, really, than RSA.
>I don't understand the argument of dictating a key over the phone. If you care about that use case, you can just a well dictate the hash of an RSA public key.
Not only dictating over phone but for example typing a SSH key over a serial line while not being able to copy-paste directly. I've had to suffer than with my RSA4096 key once and it's NOT pleasant at all.
it also means you have much less overhead for the protocol (DH and KEX with Ed25519 only need 32 bytes of space per step instead of kilobytes)
> There are still some differences. NIST provides some curves and doesn't explain much about them. You can read up how DJB choose the curves. It's a very neat and tidy process that is easy to follow and very reasonable.
You're not wrong, but to paraphrase a famous quotation: No body every got fired for following Suite B.
AES, SHA-2, and the NIST curves are approved for government crypto, and are also probably in many industry regulations. If there's ever an incident and a post-mortem audit, then it's a lot easier to explain the choice of Suite B algorithms.
Which aspect of elliptic curves would you like to understand better? The original paper for Curve25519 contains a dedicated subsection for attack models, for example, and leaves only marginal room for hidden backdoors with its detailed reasoning about curve parameter choice. The implementation of EdDH or EdDSA is specified in RFCs that are explicitly written to be "fool-proof", as others already commented.
Compare the NIST curves to RSA. For RSA we know there cannot be any backdoors. If you generate good quality primes you are in business (assuming you don't make mistakes elsewhere).
For NIST we cannot say anything about backdoors. We don't use those curves because we don't trust NIST. Not because we have any prove they are bad.
So to avoid that, there is a parameter selection process that supposedly leaves no room for backdoors, though at some CCC congress DJB described how you could use a similar process to add backdoors.
So basically, EC is based on magic. We cannot prove it is bad, we just have to hope there is no hidden magic.
Note you say 'only marginal room'. Soon the whole world will use exactly one curve. With 'only marginal room for hidden backdoors'.
I feel way more comfortable to know that with RSA what you see is what you get.
The executive summary is that while it's possible to implement and use RSA properly:
* it looks easy to implement so it's common for people to roll their own (and then it's insecure or broken), ECC look hard (though aren't necessarily) so devs are more likely to use properly vetted libraries
* because most of the parameters must be kept secret, good advice is hard to find (and good parameter selection is absolutely critical), not to mention e.g. good exponents has complexity and performance implications[0], ECC parameters are public and you can pick existing good ones.
[0] and security grows sub-linearly with parameter size: 2048-bit RSA has 112 bits of security, 4096-bit RSA has 140 bits of security
I'm just interested but it reminds me of https://facthacks.cr.yp.to/ which is a horizontal attack, finding the weakest keys in a big set of them, and batch factorization attacks. This seems more developed for RSA keys?
It implements EC with _fallback_ to RSA if EC is not available. Blame OpenSSL, I guess, because this relies on it. Even its CLI seems to be inspired by the atrocious OpenSSL CLI.
Forgive me if I can't read but I couldn't quickly find the following. Is it possible to use Opmsg as a library?
If you want to use GPG as library in your application right now, you can't. The best thing you can do is parse GPG output which is ... less-than-ideal at best and downright wrong and dangerous at worst. If one can use this as a library rather GPG that would be a huge win.
The perfect forward secrecy here seems to involve deleting a "persona". I an not sure how that is any different from doing PFS by deleting a PGP subkey. Like with PGP if you do this you lose email archived under that persona. There is no automation to re-encrypt the archive with a different key.
So I am not really sure if this has a killer feature that would make anyone want to go to the bother of abandoning PGP...
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?
> 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.
So what's the alternative, for asymmetrically encrypting arbitrary binary data?
For sending such data to others, the Latacora article suggest a tool that I've never heard of or heard recommended by other experts called "Magic Wormhole". It's a new tool that (from what I call tell) has a whole crapload of limitations and assumptions that PGP does not have: https://magic-wormhole.readthedocs.io/en/latest/welcome.html...
One of the most severe is that it apparently requires both ends to have active internet connections to transfer the data over the wire between them. As I type this, I'm visiting my parents who have 5 Mbps internet. Let's hope that file isn't big or my contact has the time and patience to wait if it is! The other is that it apparently relies on a shared password, which just takes us back to encryption before the very problem PGP was designed to solve...
For simply "encrypting files", even Latacora gives up and says "use PGP"!!
As a side note, though I agree with them that PGP is not good for secure messaging, I don't find their alternatives convincing there either. Signal and Wire don't have solid group chat capabilities that don't rely on a single central server run by a third party and don't require private information like a phone number to use. I consider that absolutely basic for a good messenger. At least PGP, though very faulty in this area, is designed to be used over existing protocols like email to make them secure, so it doesn't have the last two limitations.
Wormhole isn't new, and if you haven't heard another "expert" recommend it, you don't hang out with a lot of cryptography engineers.
The point about "simply encrypting files" is that nobody is implementing something with PGP's "encrypt-a-file" interface because it's not that useful; rather, people purposefully design modern systems with cryptography tailored to tasks, like messaging or file transfer or backup.
Your last point about PGP vs. Signal is pretty funny, as it implies that PGP has "solid group chat capabilities".
> Wormhole isn't new, and if you haven't heard another "expert" recommend it, you don't hang out with a lot of cryptography engineers.
You're right, I don't. But the earliest thing I found about Wormhole after a quick look was from 2015, which I think is pretty recent in the crypto world. Maybe I missed something.
> Your last point about PGP vs. Signal is pretty funny, as it implies that PGP has "solid group chat capabilities".
I tried to be clear about the fact that I wasn't saying that. Its benefits over Signal and Wire (but not Matrix) are that it doesn't require a central server and doesn't require any PII to sign up. I consider those crucial for anyone who has extreme security / privacy needs. PGP completely sucks for group messaging, I agree. But the alternatives suggested are simply non-starters for many use cases.
Look, my point is this: If I open my text editor and type some text, save the file and sign it with GPG with my private key to prove authorship, then I don't see how you are going to break this. In that specific sense GPG is not broken.
There are countless online puzzles or cryptography use cases based on this. I am asserting that since GPG is not broken in this specific sense, you can't just say GPG is broken "in its entirety".
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.
I finally got that when someone pointed out that the long term key is not used to encrypt the mail content - i made that leap incorrectly and went from there.
I made the change down thread - was too late to edit the original - and i hope clearly pointed out that your article did not say that
It takes me several run ups to understand most security issues and I got all excited before having my coffee that day.
How do I negotiate a session key with the email recipient? it's a single transmission? otherwise it's a one time pad perhaps - but then that defeats the point of the public key ?
would you mind expanding on this as it is an interesting area
A random key is used to encrypt the email, then that random key is asymmetrically encrypted using the recipient's public RSA key. You do not use your own key to encrypt mails to someone else. Indeed, you can send encrypted emails without even having a key of your own.
And yes thats what he says in the original latacora post.
I read the article '''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)'''
So I made the (incorrect) leap to pgp using the long term key to encrypt files. My bad.
But this does not fix the original point it seems - email is not going to be "secure" any time soon. But you can send encrypted files over email to people.
> my plaintext and my cipher are available in the wild and my key (my long term key) is effectively broken.
Wait a minute. I may have to read the Latacora article again but if we are dealing with ciphers where having a plaintext attack reveals the key, I think we're in a lot bigger trouble than I ever imagined. To be blunt I don't really believe it and it would take some explanation to convince me it's true.
Edit: OK, I think I see the problem. I believe the quote in the article is discussing the fact that the user happily quotes a message and doesn't re-encrypt it, meaning that you have accidentally leaked the plain text -- not that they key is known. So I think they are arguing that we should write apps so that it is impossible to copy the plaintext.
Since (as detailed in the reply chain) this is completely incorrect (PGP simply doesn't have this vulnerability), can you edit the comment to that effect? Otherwise this claim is a bit dangerous.
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.
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.
I would love to see a sound implementation of secure e-mail, but I also believe that such a system should not be built on top of SMTP.
Signal’s cryptography seems stellar, but to me it feels a bit weird to use instant messaging as a full replacement for electronic letters. I’m guessing here, but it would probably not be impossible to build a more traditional e-mail client on top of the Signal Protocol.
Isn't this mainly about adding a a subject metadata field an a client that just displays messages differently, enables sorting into directories and so on?
Is there a real technical difference between messaging and long form emails that I don't see?
Replacing email with a seperate 'secure email' system would probably work, at least until idiots write awful implementations of the secure-email protocols.
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.