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Set OPENSSL_CONF=X:\path_to\OpenSSL-Win64\bin\openssl.cfg
Use jgem and jbundler to install
NOTE: jRuby may need its encryption to be upgraded: http://www.oracle.com/technetwork/java/javase/downloads/jce-7-download-432124.html
For JRE7: You can find these at the Oracle Website. Download the zip file, and extract the two important files it contains: local_policy.jar and US_export_policy.jar. Move these files into your $JAVA_HOME/jre/lib/security directory.
jRuby should have the following ENV variable set: _JAVA_OPTIONS=-Xms1152m -Xmx1152m -XX:+UseConcMarkSweepGC -XX:+CMSClassUnloadingEnabled