Sebastien, JRuby isn't far from Java. This is still broken for Windows Vista. Here's the error seen when trying to install the plugin without a restart:

hudson.util.IOException2: Failed to dynamically deploy this plugin
at hudson.model.UpdateCenter$InstallationJob._run(UpdateCenter.java:1259)
at hudson.model.UpdateCenter$DownloadJob.run(UpdateCenter.java:1056)
at java.util.concurrent.Executors$RunnableAdapter.call(Unknown Source)
at java.util.concurrent.FutureTask$Sync.innerRun(Unknown Source)
at java.util.concurrent.FutureTask.run(Unknown Source)
at java.util.concurrent.ThreadPoolExecutor$Worker.runTask(Unknown Source)
at java.util.concurrent.ThreadPoolExecutor$Worker.run(Unknown Source)
at java.lang.Thread.run(Unknown Source)
Caused by: java.io.IOException: Unable to delete C:\Program Files (x86)\Jenkins\plugins\ruby-runtime\WEB-INF\lib\jruby-complete-1.6.5.jar
at hudson.Util.deleteFile(Util.java:243)
at hudson.Util.deleteRecursive(Util.java:293)
at hudson.Util.deleteContentsRecursive(Util.java:204)
at hudson.Util.deleteRecursive(Util.java:284)
at hudson.Util.deleteContentsRecursive(Util.java:204)
at hudson.Util.deleteRecursive(Util.java:284)
at hudson.Util.deleteContentsRecursive(Util.java:204)
at hudson.Util.deleteRecursive(Util.java:284)
at hudson.ClassicPluginStrategy.explode(ClassicPluginStrategy.java:411)
at hudson.ClassicPluginStrategy.createPluginWrapper(ClassicPluginStrategy.java:117)
at hudson.PluginManager.dynamicLoad(PluginManager.java:391)
at hudson.model.UpdateCenter$InstallationJob._run(UpdateCenter.java:1255)
... 7 more

The file C:\Program Files (x86)\Jenkins\plugins\ruby-runtime\WEB-INF\lib\jruby-complete-1.6.5.jar exists but Windows prevents the file from being deleted if a process is using it. It seems that Jenkins tries to load it which is why it's unable to be deleted.

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