X509 0.7

Written by hannes
Classified under: mirageossecuritytls
Published: 2019-08-15 (last updated: 2021-11-19)

Cryptographic material

Once a private and public key pair is generated (doesn't matter whether it is plain RSA, DSA, ECC on any curve), this is fine from a scientific point of view, and can already be used for authenticating and encrypting. From a practical point of view, the public parts need to be exchanged and verified (usually a fingerprint or hash thereof). This leads to the struggle how to encode this cryptographic material, and how to embed an identity (or multiple), capabilities, and other information into it. X.509 is a standard to solve this encoding and embedding, and provides more functionality, such as establishing chains of trust and revocation of invalidated or compromised material. X.509 uses certificates, which contain the public key, and additional information (in a extensible key-value store), and are signed by an issuer, either the private key corresponding to the public key - a so-called self-signed certificate - or by a different private key, an authority one step up the chain. A rather long, but very good introduction to certificates by Mike Malone is available here.

OCaml ecosystem evolving

More than 5 years ago David Kaloper and I released the initial ocaml-x509 package as part of our TLS stack, which contained code for decoding and encoding certificates, and path validation of a certificate chain (as described in RFC 5280). The validation logic and the decoder/encoder, based on the ASN.1 grammar specified in the RFC, implemented using David's asn1-combinators library changed much over time.

The OCaml ecosystem evolved over the years, which lead to some changes:

  • Camlp4 deprecation - we used camlp4 for stream parsers of PEM-encoded certificates, and sexplib.syntax to derive s-expression decoders and encoders;
  • Avoiding brittle ppx converters - which we used for s-expression decoders and encoders of certificates after camlp4 was deprecated;
  • Build and release system iterations - initially oasis and a packed library, then topkg and ocamlbuild, now dune;
  • Introduction of the result type in the standard library - we used to use [ `Ok of certificate option | `Fail of failure ];
  • No more leaking exceptions in the public API;
  • Usage of pretty-printers, esp with the fmt library val pp : Format.formatter -> 'a -> unit, instead of val to_string : t -> string functions;
  • Release of ptime, a platform-independent POSIX time support;
  • Release of rresult, which includes combinators for computation results;
  • Release of gmap, a Map whose value types depend on the key, used for X.509 extensions, GeneralName, DistinguishedName, etc.;
  • Release of domain-name, a library for domain name operations (as specified in RFC 1035) - used for name validation;
  • Usage of the alcotest unit testing framework (instead of oUnit).

More use cases for X.509

Initially, we designed and used ocaml-x509 for providing TLS server endpoints and validation in TLS clients - mostly on the public web, where each operating system ships a set of ~100 trust anchors to validate any web server certificate against. But once you have a X.509 implementation, every authentication problem can be solved by applying it.

Authentication with path building

It turns out that the trust anchor sets are not equal across operating systems and versions, thus some web servers serve sets, instead of chains, of certificates - as described in RFC 4158, where the client implementation needs to build valid paths and accept a connection if any path can be validated. The path building was initially in 0.5.2 slightly wrong, but fixed quickly in 0.5.3.

Fingerprint authentication

The chain of trust validation is useful for the open web, where you as software developer don't know to which remote endpoint your software will ever connect to - as long as the remote has a certificate signed (via intermediates) by any of the trust anchors. In the early days, before let's encrypt was launched and embedded as trust anchors (or cross-signed by already deployed trust anchors), operators needed to pay for a certificate - a business model where some CAs did not bother to check the authenticity of a certificate signing request, and thus random people owning valid certificates for microsoft.com or google.com.

Instead of using the set of trust anchors, the fingerprint of the server certificate, or preferably the fingerprint of the public key of the certificate, can be used for authentication, as optionally done since some years in jackline, an XMPP client. Support for this certificate / public key pinning was added in x509 0.2.1 / 0.5.0.

Certificate signing requests

Until x509 0.4.0 there was no support for generating certificate signing requests (CSR), as defined in PKCS 10, which are self-signed blobs containing a public key, an identity, and possibly extensions. Such as CSR is sent to the certificate authority, and after validation of ownership of the identity and paying a fee, the certificate is issued. Let's encrypt specified the ACME protocol which automates the proof of ownership: they provide a HTTP API for requesting a challenge, providing the response (the proof of ownership) via HTTP or DNS, and then allow the submission of a CSR and downloading the signed certificate. The ocaml-x509 library provides operations for creating such a CSR, and also for signing a CSR to generate a certificate.

Mindy developed the command-line utility certify which uses these operations from the ocaml-x509 library and acts as a swiss-army knife purely in OCaml for these required operations.

Maker developed a let's encrypt library which implements the above mentioned ACME protocol for provisioning CSR to certificates, also using our ocaml-x509 library.

To complete the required certificate authority functionality, in x509 0.6.0 certificate revocation lists, both validation and signing, was implemented.

Deploying unikernels

As described in another post, I developed albatross, an orchestration system for MirageOS unikernels. This uses ASN.1 for internal socket communication and allows remote management via a TLS connection which is mutually authenticated with a X.509 client certificate. To encrypt the X.509 client certificate, first a TLS handshake where the server authenticates itself to the client is established, and over that connection another TLS handshake is established where the client certificate is requested. Note that this mechanism can be dropped with TLS 1.3, since there the certificates are transmitted over an already encrypted channel.

The client certificate already contains the command to execute remotely - as a custom extension, being it "show me the console output", or "destroy the unikernel with name = YYY", or "deploy the included unikernel image". The advantage is that the commands are already authenticated, and there is no need for developing an ad-hoc protocol on top of the TLS session. The resource limits, assigned by the authority, are also part of the certificate chain - i.e. the number of unikernels, access to network bridges, available accumulated memory, accumulated size for block devices, are constrained by the certificate chain presented to the server, and currently running unikernels. The names of the chain are used for access control - if Alice and Bob have intermediate certificates from the same CA, neither Alice may manage Bob's unikernels, nor Bob may manage Alice's unikernels. I'm using albatross since 2.5 years in production on two physical machines with ~20 unikernels total (multiple users, multiple administrative domains), and it works stable and is much nicer to deal with than scp and custom hacked shell scripts.

Why 0.7?

There are still some missing pieces in our ocaml-x509 implementation, namely modern ECC certificates (depending on elliptic curve primitives not yet available in OCaml), RSA-PSS signing (should be straightforward), PKCS 12 (there is a pull request, but this should wait until asn1-combinators supports the ANY defined BY construct to cleanup the code), ... Once these features are supported, the library should likely be named PKCS since it supports more than X.509, and released as 1.0.

The 0.7 release series moved a lot of modules and function names around, thus it is a major breaking release. By using a map instead of lists for extensions, GeneralName, ..., the API was further revised - invariants that each extension key (an ASN.1 object identifier) may occur at most once are now enforced. By not leaking exceptions through the public interface, the API is easier to use safely - see let's encrypt, openvpn, certify, tls, capnp, albatross.

I intended in 0.7.0 to have much more precise types, esp. for the SubjectAlternativeName (SAN) extension that uses a GeneralName, but it turns out the GeneralName is as well used for NameConstraints (NC) in a different way -- IP in SAN is an IPv4 or IPv6 address, in CN it is the IP/netmask; DNS is a domain name in SAN, in CN it is a name starting with a leading dot (i.e. ".example.com"), which is not a valid domain name. In 0.7.1, based on a bug report, I had to revert these variants and use less precise types.


The work on X.509 was sponsored by OCaml Labs. You can support our work at robur by a donation, which we will use to work on our OCaml and MirageOS projects. You can also reach out to us to realize commercial products.

I'm interested in feedback, either via twitter hannesm@mastodon.social or via eMail.