I just checked in a few updates to my openssl branch for JRuby. Boy is it tricky getting everything right. It seems like every DER format Java crypto emits differs from the OpenSSL DER output. And it's really incompatible. As an example I have been forced to reimplement the DER dumping for X509 certificates myself, and that's not the only place.
But the work is actually going forward; as fast as I can make it when I'm only doing this in my spare time and my regular work takes lots of time right now. I can't say for sure when it will be finished or usable, but I know for a fact that most of the MRI tests run now. What's missing is PKCS#7, X509 CRL's and X509 cert-stores, plus the regular SSL socket support. Not much, compared to what actually works.
But that leads to me to two issues. We have recently agreed that OpenSSL support will require BouncyCastle and Java 5. There is really no other way to get this working. 1.4.2 is fine for basic Digest support and some of the RSA/DSA support, but Java is sorely lacking in the ASN.1 and X509 department. Nothing whatsoever. Which is why we need BouncyCastle, which is fairly complete. I have only been forced to reimplement one or two central classes. Quite good. But SSL support is another story. As you may know, 1.4.2 has SSLSocket and SSLServerSocket. The problem is this: they aren't any good. As a first, they are blocking, and there isn't any support in 1.4.2 for NIO SSL sockets. Whoopsie. Which explains the requirement on Java 5. Tiger adds the SSLEngine class which can be used to implement NIO SSL, with the caveat that it heightens complexity. I have only taken a cursory look at this yet. Right now I want the other stuff working first, since there are so many dependencies on them.
But it's really going forward. Now, if I only had this as my day job, this would be finished in a few days... Alas, that's not the way it is. Expect further updates in a week or two.