great that there is someone with osgi knowhow looking at that ;) but I have the feeling you missed the current state of osgi:
$ mvn -Pcomplete will run the osgi IT which is now in maven/jruby-complete/src/it/osgi-test which is just copy and paste of the old code with some adjustments to get it pass. whether passing that test means a lot I do not know. the bouncy-castle jars are bundled within the META-INF/jruby.home along with a number of other jars - not sure what the issue there is but any gem with jars will have the same issue - the jruby-classloader loading a vendored jar. so it would be great to use the integration test from jruby-complete as a starting point. - christian