Tag: pgpainless

When I first thought about signature verification in OpenPGP I thought “well, it cannot be that hard, right?”. In the end all you got to do is check if a signature was made by the given key and if that signature checks out (is cryptographically correct). Oh boy, was I wrong.

The first major realization that struck me was that there are more than just two factors involved in the signature verification process. While the first two are pretty obvious – the signature itself and the key that created it – another major factor is played by the point in time at which a signature is being verified. OpenPGP keys are changing over the course of their lifespan. Subkeys may expire or be revoked for different reasons. A subkey might be eligible to create valid signatures until its binding signature expires. From that point in time all new signatures created with that key must be considered invalid. Keys can be rebound, so an expired key might become valid again at some point, which would also make (new) signatures created with it valid once again.

But what does it mean to rebind a key? How are expiration dates set on keys and what role plays the reason of a revocation?

The answer to the first two questions is – Signatures!

OpenPGP keys consist of a set of keys and subkeys, user-id packets (which contain email addresses and names and so forth) and lastly a bunch of signatures which tie all this information together. The root of this bunch is the primary key – a key with the ability to create signatures, or rather certifications. Signatures and certifications are basically the same, they just have a different semantic meaning, which is quite an important detail. More to that later.

The main use of the primary key is to bind additional data to it. First and foremost user-id packets, which can (along with the primary keys key-ID) be used to identify the key. Alice might for example have a user-id packet on her key which contains her name and email address. Keys can have more than one user-id, so Alice might also have an additional user-id packet with her work-email or her chat address added to the key.

But simply adding the packet to the key is not enough. An attacker might simply take her key, change the email address and hand the modified key to Bob, right? Wrong. Signatures Certifications to the rescue!

   Primary-Key
      [Revocation Self Signature]
      [Direct Key Signature...]
      [User ID [Signature ...] ...]
      [User Attribute [Signature ...] ...]
      [[Subkey [Binding-Signature-Revocation]
              Subkey-Binding-Signature ...] ...]

Information is not just loosely appended to the key. Instead it is cryptographically bound to it by the help of a certification. Certifications are signatures which can only be created by a key which is allowed to create certifications. If you take a look at any OpenPGP (v4) key, you will see that most likely every single primary key will be able to create certifications. So basically the primary key is used to certify that a piece of information belongs to the key.

The same goes for subkeys. They are also bound to the primary key with the help of a certification. Here, the certification has a special type and is called “subkey binding signature”. The concept though is mostly the same. The primary key certifies that a subkey belongs to it by help of a signature.

Now it slowly becomes complicated. As you can see, up to this point the binding relations have been uni-directional. The primary key claims to be the dominant part of the relation. This might however introduce the risk of an attacker using a primary key to claim ownership of a subkey which was used to make a signature over some data. It would then appear as if the attacker is also the owner of that signature. That’s the reason why a signing-capable subkey must somehow prove that it belongs to its primary key. Again, signatures to the rescue! A subkey binding signature that binds a signing capable subkey MUST contain a primary key binding signature made by the subkey over the primary key. Now the relationship is bidirectional and attacks such as the one mentioned above are mitigated.

So, about certifications – when is a key allowed to create certifications? How can we specify what capabilities a key has?

The answer are Signature… Subpackets!
Those are some pieces of information that are added into a signature that give it more semantic meaning aside from the signature type. Examples for signature subpackets are key flags, signature/key creation/expiration times, preferred algorithms and many more. Those subpackets can reside in two areas of the signature. The unhashed area is not covered by the signature itself, so here packets can be added/removed without breaking the signature. The hashed area on the other hand gets its name from the fact that subpackets placed here are taken into consideration when the signature is being calculated. They cannot be modified without invalidating the signature.

So the unhashed area shall only contain advisory information or subpackets which are “self-authenticating” (meaning information which is validated as a side-effect of validating the signature). An example of a self-authenticating subpacket would be the issuers-id packet, which contains the key-id of the key that created the signature. This piece of information can be verified by checking if the denominated key really created the signature. There is no need to cover this information by the signature itself.

Another really important subpacket type is the key flags packet. It contains a bit-mask that declares what purpose a key can be used for, or rather what purpose the key is ALLOWED to be used for. Such purposes are encryption of data at rest, encryption of data in transit, signing data, certifying data, authentication. Additionally there are key flags indicating that a key has been split by a key-splitting mechanism or that a key is being shared by more than one entity.

Each signature MUST contain a signature creation time subpacket, which states at which data and time a signature was created. Optionally a signature might contain a signature expiration time subpacket which denotes at which point in time a signature expires and becomes invalid. So far so good.

Now, those subpackets can also be placed on certifications, eg. subkey binding signatures. If a subkey binding signature contains a key expiration time subpacket, this indicates that the subkey expires at a certain point in time. An expired subkey must not be used anymore and signatures created by it after it has been expired must be considered invalid. It gets even more complicated if you consider, that a subkey binding signature might contain a key expiration time subpacket, along with a signature expiration time subpacket. That could lead to funny situations. For example a subkey might have two subkey binding signatures. One simply binds the key indefinitely, while the second one has an expiration time. Here the latest binding signature takes precedence, meaning the subkey might expire at lets say t+3, while at t+5 the signature itself expires, meaning that the key regains validity, as now the former binding signature is “active” again.

Not yet complicated enough? Consider this: Whether or not a key is eligible to create signatures is denoted by the key flags subpacket which again is placed in a signature. So when verifying a signature, you have to consult self-signatures on the signing key to see if it carries the sign-data key flag. Furthermore you have to validate that self-signature and check if it was created by a key carrying the certify-other key flag. Now again you have to check if that signature was created by a key carrying the certify-other key flag (given it is not the same (primary) key). Whew.

Lastly there are key revocations. If a key gets lost or stolen or is simply retired, it can be revoked. Now it depends on the revocation reason, what impact the revocation has on past and/or future signatures. If the key was revoked using a “soft” revocation reason (key has not been compromised), the revocation is mostly handled as if it were an expiration. Past signatures are still good, but the key must no longer be used anymore. If it however has a “hard” revocation reason (or no reason at all) this could mean that the key has been lost or compromised. This means that any signature (future and past) that was made by this key has now to be considered invalid, since an attacker might have forged it.

Now, a revocation can only be created by a certification capable key, so in order to check if a revocation is valid, we have to check if the revoking key is allowed to revoke this specific subkey. Permitted revocation keys are either the primary key, or an external key denoted in a revocation key subpacket on a self-signature. Can you see why this introduces complexity?

Revocation signatures have to be handled differently from other signatures, since if the primary key is revoked, is it eligible to create revocation signatures in the first place? What if an external revocation key has been revoked and is now used to revoke another key?

I believe the correct way to tackle signature validity is to first evaluate the key (primary and subkeys) at signature creation time. Evaluating the key at a given point in time tn means we reject all signatures made after tn (except hard revocations) as those are not yet valid. Furthermore we reject all signatures that are expired a tn as those are no longer valid. Furthermore we remove all signatures that are superseded by another more recent signature. We do this for all signatures on all keys in the “correct” order. What we are left with is a canonicalized key ring, which we can now use to verify the signature in question with.

So lets try to summarize every step that we have to take in order to verify a signatures validity.

• First we have to check if the signature contains a creation time subpacket. If it does not, we can already reject it.
• Next we check if the signature is expired by now. If it is, we can again reject.
• Now we have to evaluate the key ring that contains the signatures signing key at the time at which the signature was created.
  • Is the signing key properly bound to the key ring?
    • Was is created before the signature?
    • Was it bound to the key ring before the signature was made?
    • Is the binding signature not expired?
    • Is the binding signature not revoked?
    • Is the subkey binding signature carrying a valid primary key binding signature?
    • Are the binding signatures using acceptable algorithms?
  • Is the subkey itself not expired?
  • Is the primary key not expired?
  • Is the primary key not revoked?
  • Is the subkey not revoked?
• Is the signing key capable of creating signatures?
• Was the signature created with acceptable algorithms? Reject weak algorithms like SHA-1.
• Is the signature correct?

Lastly of course, the user has to decide if the signing key is trustworthy or not, but luckily we can leave this decision up to the user.

As you can see, this is not at all trivial and I’m sure I missed some steps and/or odd edge cases. What makes implementing this even harder is that the specification is deliberately sparse in places. What subpackets are allowed to be placed in the unhashed area? What MUST be placed in the hashed area instead? Furthermore the specification contains errors which make it even harder to get a good picture of what is allowed and what isn’t. I believe what OpenPGP needs is a document that acts as a guide to implementors. That guide needs to specify where and where not certain subpackets are to be expected, how a certain piece of semantic meaning can be represented and how signature verification is to be conducted. It is not desirable that each and every implementor has to digest the whole specification multiple times in order to understand what steps are necessary to verify a signature or to select a valid key for signature creation.

Did you implement signature verification in OpenPGP? What are your thoughts on this? Did you go through the same struggles that I do?

Lastly I want to give a shout-out to the devs of Sequoia-PGP, which have a pretty awesome test suite that covers lots and lots of edge-cases and interoperability concerns of implementations. I definitely recommend everyone who needs to work with OpenPGP to throw their implementation against the suite to see if there are any shortcomings and problems with it.