I'm having a similar issue. This works on my Windows 8.1 64bit laptop, but not on a Windows 2008 64bit server. The error message I'm getting is below.
{:timestamp=>"2015-06-03T15:48:00.274000+1200", :message=>"Windows Event Log error: Invoke of: NextEvent\nSource: SWbemEventSource\nDescription: Timed out \n\n[\"org.racob.com.Dispatch.invokev(Native Method)\", \"org.racob.com.Dispatch.invokev(Dispatch.java:243)\", \"org.racob.com.Dispatch.callN(Dispatch.java:187)\", \"org.jruby.ext.win32ole.RubyWIN32OLE.invokeMethodOrGet(RubyWIN32OLE.java:205)\", \"org.jruby.ext.win32ole.RubyWIN32OLE.method_missing(RubyWIN32OLE.java:113)\", \"org.jruby.ext.win32ole.RubyWIN32OLE$INVOKER$i$0$0$method_missing.call(RubyWIN32OLE$INVOKER$i$0$0$method_missing.gen)\", \"org.jruby.internal.runtime.methods.JavaMethod$JavaMethodN.call(JavaMethod.java:677)\", \"org.jruby.runtime.Helpers$MethodMissingMethod.call(Helpers.java:452)\", \"org.jruby.internal.runtime.methods.DynamicMethod.call(DynamicMethod.java:210)\", \"org.jruby.runtime.callsite.CachingCallSite.callMethodMissing(CachingCallSite.java:401)\", \"org.jruby.runtime.callsite.CachingCallSite.cacheAndCall(CachingCallSite.java:323)\", \"org.jruby.runtime.callsite.CachingCallSite.call(CachingCallSite.java:170)\", \"org.jruby.ast.CallOneArgNode.interpret(CallOneArgNode.java:57)\", \"org.jruby.ast.DAsgnNode.interpret(DAsgnNode.java:110)\", \"org.jruby.ast.NewlineNode.interpret(NewlineNode.java:105)\", \"org.jruby.ast.BlockNode.interpret(BlockNode.java:71)\", \"org.jruby.evaluator.ASTInterpreter.INTERPRET_BLOCK(ASTInterpreter.java:112)\", \"org.jruby.runtime.Interpreted19Block.evalBlockBody(Interpreted19Block.java:206)\", \"org.jruby.runtime.Interpreted19Block.yield(Interpreted19Block.java:157)\", \"org.jruby.runtime.Interpreted19Block.yieldSpecific(Interpreted19Block.java:130)\", \"org.jruby.runtime.Block.yieldSpecific(Block.java:111)\", \"org.jruby.RubyKernel.loop(RubyKernel.java:1507)\", \"org.jruby.RubyKernel$INVOKER$s$0$0$loop.call(RubyKernel$INVOKER$s$0$0$loop.gen)\", \"org.jruby.runtime.callsite.CachingCallSite.cacheAndCall(CachingCallSite.java:316)\", \"org.jruby.runtime.callsite.CachingCallSite.callBlock(CachingCallSite.java:145)\", \"org.jruby.runtime.callsite.CachingCallSite.callIter(CachingCallSite.java:154)\", \"org.jruby.ast.FCallNoArgBlockNode.interpret(FCallNoArgBlockNode.java:32)\", \"org.jruby.ast.NewlineNode.interpret(NewlineNode.java:105)\", \"org.jruby.ast.BlockNode.interpret(BlockNode.java:71)\", \"org.jruby.ast.RescueNode.executeBody(RescueNode.java:221)\", \"org.jruby.ast.RescueNode.interpret(RescueNode.java:116)\", \"org.jruby.ast.BeginNode.interpret(BeginNode.java:83)\", \"org.jruby.ast.NewlineNode.interpret(NewlineNode.java:105)\", \"org.jruby.ast.BlockNode.interpret(BlockNode.java:71)\", \"org.jruby.evaluator.ASTInterpreter.INTERPRET_METHOD(ASTInterpreter.java:74)\", \"org.jruby.internal.runtime.methods.InterpretedMethod.call(InterpretedMethod.java:182)\", \"org.jruby.internal.runtime.methods.DefaultMethod.call(DefaultMethod.java:203)\", \"org.jruby.runtime.callsite.CachingCallSite.cacheAndCall(CachingCallSite.java:326)\", \"org.jruby.runtime.callsite.CachingCallSite.call(CachingCallSite.java:170)\", \"org.jruby.ast.CallOneArgNode.interpret(CallOneArgNode.java:57)\", \"org.jruby.ast.NewlineNode.interpret(NewlineNode.java:105)\", \"org.jruby.ast.RescueNode.executeBody(RescueNode.java:221)\", \"org.jruby.ast.RescueNode.interpret(RescueNode.java:116)\", \"org.jruby.ast.BeginNode.interpret(BeginNode.java:83)\", \"org.jruby.ast.NewlineNode.interpret(NewlineNode.java:105)\", \"org.jruby.ast.BlockNode.interpret(BlockNode.java:71)\", \"org.jruby.ast.EnsureNode.interpret(EnsureNode.java:96)\", \"org.jruby.evaluator.ASTInterpreter.INTERPRET_METHOD(ASTInterpreter.java:74)\", \"org.jruby.internal.runtime.methods.InterpretedMethod.call(InterpretedMethod.java:182)\", \"org.jruby.internal.runtime.methods.DefaultMethod.call(DefaultMethod.java:203)\", \"org.jruby.runtime.callsite.CachingCallSite.cacheAndCall(CachingCallSite.java:326)\", \"org.jruby.runtime.callsite.CachingCallSite.call(CachingCallSite.java:170)\", \"org.jruby.ast.FCallOneArgNode.interpret(FCallOneArgNode.java:36)\", \"org.jruby.ast.NewlineNode.interpret(NewlineNode.java:105)\", \"org.jruby.evaluator.ASTInterpreter.INTERPRET_BLOCK(ASTInterpreter.java:112)\", \"org.jruby.runtime.Interpreted19Block.evalBlockBody(Interpreted19Block.java:206)\", \"org.jruby.runtime.Interpreted19Block.yield(Interpreted19Block.java:194)\", \"org.jruby.runtime.Interpreted19Block.call(Interpreted19Block.java:125)\", \"org.jruby.runtime.Block.call(Block.java:101)\", \"org.jruby.RubyProc.call(RubyProc.java:290)\", \"org.jruby.RubyProc.call(RubyProc.java:228)\", \"org.jruby.internal.runtime.RubyRunnable.run(RubyRunnable.java:99)\", \"java.lang.Thread.run(Unknown Source)\"]", :level=>:error}