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I was reading about Protonmail's system and I couldn't find an anwser to something. In PGP communication is encrypted using assymetric cryptography: public and private keys. If you want to send something securely to a recipient you use they public key of the recipient.

To my understanding: in nowadays internet systems to gain the public key of someone usually you (or the client software) looks for the public key from a keyserver. If so this system prone to MITM attacks, in other words it is a single point of failure.

Am I correct that this is the way public keys are distributed usually? Through a central publicly available server? I know TLS/SSL during keyexchange can prevent the attack, but that PKI system also has it's centralized aspects so, I am asking disregarding that.

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Actually, the naiive approach of just grabbing a key from a keyserver isn't vulnerable so much to a man-in-the-middle attack as to a poisoning attack.

In a poisoning attack, an attacker provides an alternative piece of information, in this case a public key, and somehow tricks you into using that instead of the real one.

In a man-in-the-middle attack, the attacker sits (logically or physically) between you and the system, or recipient, you're talking to, appearing to each end point as the other end point.


That said, you are correct that keys from a key server cannot be trusted immediately. They do need to be validated somehow.

In the PGP/OpenPGP/RFC4880 trust model, that validation is primarily via key fingerprints and signatures.

For the sake of an example, let's say Alice wants to communicate securely with Bob, but neither of them have ever met, nor is it likely that they will be able to meet. Both, however, have access to an OpenPGP implementation and can upload public keys to key servers. Both have gone through the preliminaries of setting up e-mail accounts, creating key pairs associated with those e-mail addresses, and uploading their respective public key to a shared key server.

So can Carol, who would like to be able to read what Alice and Bob are sending to each other. Carol has also somehow gained access to Bob's e-mail account. (Maybe Bob used a weak password.)

The easy way, if Alice is able to communicate with Bob out of band, is for Alice to contact Bob using some other medium, and ask him for his public key fingerprint. If that matches the key that Alice has, and Alice can trust that the person responding is actually Bob and not Carol, then she can very likely trust the key to belong to Bob.

Even if she can't, however, there is a way.

Bob isn't alone in this world. While Alice can't meet Bob in person, a number of other people can and have. Those people can sign Bob's key, which is a statement that they have verified Bob's identity, and that the key they are signing actually belongs to Bob, and not to an imposter. Carol can't get those people to sign her key as belonging to Bob, because that would raise questions on the form "hey Bob, why're you changing keys?", ideally asked in ways Carol cannot control. For example, Dave might pull out his phone book and call Bob on the telephone to ask, since he recognizes Bob's voice, or might ask him at work, because they work for the same company.

So Alice can look at the set of signatures on the key purporting to be Bob's, and then the set of signatures on those keys, and so on. The purpose here is to trace the signatures back to a key Alice trusts, either because she has verified it herself, or because it's a widely trusted key in the community. (For example, the widely distributed official key of the creator of the software, or that of someone associated with a large free software project, can likely be trusted if its fingerprint can be verified.)

Why not just look at the signatures themselves? For one thing, nothing prevents Carol from creating keys and signatures that appear at first glance exactly like the signatures on Bob's actual key. But while Carol can create a trust chain among the keys she create herself, she cannot anchor that trust chain elsewhere. So the trust chain might eventually lead to a key purporting to belong to, say, Werner Koch or Phil Zimmermann, but Carol can't actually anchor the trust chain there because presumably Werner Koch or Phil Zimmermann are very careful about verifying the identity of the owners of the keys that they sign, and the keys that the trust chain leads to wouldn't match their official keys. Finding a chain of signatures leading back to a high-profile key which can be validated as belonging to that individual means it is very likely that the key one started out with has not been falsified.

Alice can also ask others for the fingerprints of those anchoring keys. If multiple people agree that Koch's key has a certain fingerprint, and this matches the one she has, that significantly increases the trustworthiness of Alice's copy of that key.

Yes, there is a fair bit of work to be done if Alice wants to do this properly. That's the price one has to pay for not having a set of super-trusted keys at the root of every trust hierarchy, the way the TLS CA ecosystem (as used by web browsers) works. The flip side of that coin is that every user can decide which keys they actually trust to sign other keys.

Once Alice has verified that Bob's key is legitimate, she'd usually sign it locally (add a non-exportable signature of her own) to it. It'd be non-exportable because she hasn't actually verified the identity of the key holder, so she doesn't want to tell others about that and thus degrading the trustworthiness of her actual key signatures, but she does want to indicate to herself and to the software on her system that she has done some degree of verification of the key, thereby silencing any "this key isn't trusted!" warnings.

Simple, isn't it?

  • Yes, very nice, thank you. I have actually read something about this web of trust, and I understood it as you have understandably described it. But I don't know if this system is used in the mainstream at all or did it just stay a theoretical system? – Najib Jul 25 at 22:48
  • So is it actually, this signing of other users' keys is something that happens behind the scenes when using PGP encrypted emailing? Or is there any email service/client that lets me do this? – Najib Jul 25 at 22:53
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    @Najib Any application which does read/write operations on PGP keys should allow you to sign a key, assuming that a key suitable for key signing is available. And the web of trust is quite real, but unrelated to signing a particular message that is being transmitted. Key signature validation can perhaps be said to happen "behind the scenes" in the software, but key signing is very much a deliberate act. – a CVn Jul 26 at 8:38
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You seem to instinctively understand that an out of band trust model is important.

With PKI, your OS/Browser/Institution provides, at install or via MDM/GP, you with a list of "Trusted"(deserved or not) CAs that your system will use to extend into a tree of trusted keys/certs.

With PGP/GPG, the developers don't ask you to implicitly trust any one who they trust or who paid enough. Fingerprints are your out of band method for building up your own 1st tier of trust. After that you can define if only a single signature is sufficient to extend that trust tree/web or not.

Yes. Building your own 1st tier of trust is more work.

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Am I correct that this is the way public keys are distributed usually? Through a central publicly available server?

Yes you use a public key server.MIT public key server is a popular one for that

To my understanding: in nowadays internet systems to gain the public key of someone usually you (or the client software) looks for the public key from a keyserver. If so this system prone to MITM attacks, in other words it is a single point of failure.

Well That's certainly not easy but not impossible either

Yes you might be right.If an attacker could supply you with his own public key and then gain the encrypted data he could decrypt it using his private key which is precisely why there is mechanism built in to check if the public key belongs to your friend by using the --fingerprint option in GPG

Here is the article that shows how to

Now ofcourse the fingerprint will have be send in some way as well.There are as far as i know two ways to do this.

  1. Sign it with the receivers public key (receiver being the person that gets the public key)

    or

  2. create an out of band channel.

  • Thank you. Yes I know about the fingerprint, but that also has to be exchanged somehow. Obviously then it is much more difficult to gain control as an attacker. Reason I am asking this, maybe obvious thing, is because I think that a distributed trustless system could solve these problems such as a distributed ledger like blockchains. There are actually pretty good research work f.ex. from the RWOT team on this issue if anyone wants to look it up. But yeah, I think the next step in PGP and GPG ( and even PKI) would be an infrastructure like that. It is my humble opinion tough. – Najib Jul 25 at 17:12
  • @Najib Yeah i get your point the fingerprint would have to send as well.I guess you would create a disposable channel for sending that.I mean even the NSA must have some limits i guess. – Vipul Nair Jul 25 at 17:23

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