@yomimono or @hannesm surely know if people have tried crowbar on the BTC Piñata.
– @kensan@mastodon.social
tl;dr - yes, and it seems that ocaml-x509 is not trivially easy to trick.
Background
The Bitcoin Piñata
In 2015 David Kaloper-Mersinjak and Hannes Mehnert released ocaml-tls, an implementation of TLS (formerly known as SSL) written fully in OCaml. A full writeup of the stack is available in their Usenix Security 2015 paper, and as a series of blog posts on mirage.io. To accompany the release they also deployed a fully-automated bug bounty for the security stack – the bitcoin piñata.
The piñata will establish TLS connections only with endpoints presenting a certificate signed by its own, undisclosed certificate authority, but allows an attacker to easily listen to the encrypted traffic. The piñata always sends the same plaintext in such a connection: the private key to a wallet containing approximately 10 bitcoin. If the attacker can decrypt the ciphertext, or trick the piñata into negotiating a TLS connection with another host and disclosing the key, the information (and therefore the money) is theirs.
Crowbar
Crowbar is a library for writing tests. It combines a property-based API (like QuickCheck) with a coverage-driven generator of test cases (like the fuzzer American Fuzzy Lop). Crowbar tries to find counterexamples to stated properties by prioritizing the generation of test cases which touch more code. It is very good at finding counterexamples.
Testing ocaml-x509
TLS connections are usually authenticated via X509 certificates. ocaml-tls uses ocaml-x509 for this purpose, which is written as a standalone library. There is a clear separation of concerns between ocaml-x509 and ocaml-tls, and a straightforward API for certificate operations in ocaml-x509; both features help tremendously in writing tests for certificate handling.