From the standpoint of OSSL (Ruby’s OpenSSL binding), 1.9.3 is a small release; bug fixes, performance improvements, official OpenSSL 1.0.0 support and a few API enhancements. We had a new digital time-stamp and ASN.1 Template(DSL) implementation presented by Martin Boßlet, but we could not merge those bleeding-edge new features into 1.9.3, since there's no Ruby developer who can review it. It was quite obvious for us to ask him to be a maintainer of OSSL, as an expert in crypto and network security.
Since then, he helped us to clean up lots of OSSL issues piled on our issue tracker, by fixing SEGV bugs, consulting with users, and tailoring the build system to fit OpenSSL versions/variants. Though he discreetly didn’t merge his new feature implementations into 1.9.3, it seems clear that you can utilize those at the next release.
OSSL is the best language binding implementation of OpenSSL in the way of offering most OpenSSL features through an easy API with some help from Ruby. Without Martin Boßlet's help, we wouldn't see these new features for quite a while. Though network security is a moving target, now I’m optimistic about the prospects of those Ruby features.