Ruby compiled files, ISEQs, are made not with Ruby coming with RMS. We make it with separate RubyWin/RubyMac executable based on our own modified Ruby codebase, which is same as Ruby VM runing on device, currently 2.3.4.
egghead we compile with same ruby version we use inside mobile app (2.3.4) so it should not be the reason. The ruby version shipped in Windows installer is only needed to run rake scripts ( and you don't have to install it if you already have new version - you can just install gems to your ruby. ) Please share your files - source, configuration etc. We'll reproduce it on our side.