when I install the default gems:
krypt, jruby-openssl, bouncy-castle-java
tell bundler via the Gemfile to "use" them, see Gemfile from gist below. this will lead with

Bundler.require
require 'openssl'

to
NameError: uninitialized constant OpenSSL::Digest::OPENSSL_VERSION_NUMBER

the same happens with a fresh rails application, add those gems from the gist to the Gemfile and start rails

$ jruby -S rails server

and it fails with the same error. the workaround here is to add a require 'openssl' before the Bundler.require statement.

the gist gives the steps to reproduce it
https://gist.github.com/anonymous/9394738

the background is the websphere rails app which sees the same errors, all loosely related to jruby/warbler#238, jruby/warbler#241, #1119 #1435 and all regarding websphere