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I found an issue with jruby debugging in Vista 64. It seems like org.rubyforge.debugcommons.Util class dosn't parse the path properly in certain circumstances. I did a default install of jdk/netbeans and tried to debug a test program. However netbeans couldn't launch the debugger it issued the following error \java\jdk1.6.0_07 was unexpected (or somthing simmilar) As it turns out Vista64 use C:\Program Files (x86)\ as the default install directory for 32 bit apps, and my guess is that parsing goes wrong on the (x86) part. As a workaround I installed the jdk to c:\java\jdk1.6.0_07 instead and i everything worked fine.
Thanks for filing, will take a look at it.