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Summer of Code: The plan. Act 1: OpenPGP


OpenPGP (know as RFC4880) defines a format for encrypted and signed data, as well as encryption keys and signatures.

My main problem with the specification is, that it is very noisy. The document is 90 pages long and describes every aspect an implementer needs to know about, from how big numbers are stored, over which magic bits and bytes are in use to mark special regions in a packet, to recommendations about used algorithms. Since I’m not going to write a crypto library from scratch, the first step I have to take is to identify which parts are important for me as a user of a – lets call it mid-level-API – and which parts I can ignore. You can see this posting as kind of an hopefully somewhat entertaining piece of jotting paper which I use to note down important parts of the spec while I go through the document.

Lets start to create a short TL;DR of the OpenPGP specification.
The basic process of creating an encrypted message is as follows:

  • The sender provides a plaintext message
  • That message gets encrypted with a randomly generated symmetric key (called session key)
  • The session key then gets encrypted for each recipients public key and the resulting block of data gets prepended to the previously encrypted message

As you can see, an OpenPGP message consists of multiple parts. Those are called sub-packets. There is a pretty respectable number of sub-packet types specified in the RFC. Many of them are not very interesting, so lets identify the few which are relevant for our project.

  • Public-Key Encrypted Session Key Packets
    Those packets represent a session key encrypted with the public key of a recipient.
  • Signature Packets
    Digital signatures are used to provide authenticity. If a piece of data is signed using the secret key of the sender, the recipient is able to verify its origin and authenticity. There is a whole load of different signature sub-packets, so for now we just acknowledge their existence without going into too much detail.
  • Compressed Data Packets
    OpenPGP provides the feature of compressing plaintext data prior to encrypting it. This might come in handy, since encrypting files or messages adds quite a bit of overhead. Compressing the original data can compensate that effect a little bit.
  • Symmetrically Encrypted Data Packets
    This packet type represents data which has been encrypted using a symmetric key (in our case the session key).
  • Literal Data Packets
    The original message we want to encrypt is referred to as literal data. The literal data packet consists of metadata like encoding of the original message, or filename in case we want to encrypt a file, as well as – of course – the data itself.
  • ASCII Armor (not really a Packet)
    Encrypted data is represented in binary form. Since one big use case of OpenPGP encryption is in Email messaging though, it is necessary to bring the data into a form which can be transported safely. The ASCII Armor is an additional layer which encodes the binary data using Base64. It also makes the data identifiable for humans by adding a readable header and footer. XEP-0373 forbids the use of ASCII Armor though, so lets focus on other things instead :D

Those packet types can be nested, as well as concatenated in many different ways. For example, a common constellation would consist of a Literal Data Packet of our original message, which is, along with a Signature Packet, contained inside of a Compressed Data Packet to save some space. The Compressed Data Packet is nested inside of a Symmetrically Encrypted Data Packet, which lives inside of an OpenPGP message along with one or more Public-Key Encrypted Session Key Packets.

Each packet carries additional information, for example which compression algorithm is used in the Compressed Data Packet. We will not focus on those details, as we assume that the libraries we use will already handle those specifics for us.

OpenPGP also specifies a way to store and exchange keys. In order to be able to receive encrypted messages, a user must distribute their keys to other users. A key can carry a lot of additional information, like identities and signatures of other keys. Signatures are used to create trust networks like the web of trust, but we will most likely not dive deeper into that.

Signatures on keys can also be used to create key hierarchies like super keys and sub-keys. It still has to be determined, if and how those patterns will be reflected in my code. I can imagine it would be useful to only have sub-keys on mobile devices, while the main super key is hidden away from the orcs in a bunker somewhere, but I also think that it would be a rather complicated task to add support for sub-keys to my project. We will see ;)

That’s it for Part 1 of my sighting of the OpenPGP RFC.

Happy Hacking!

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