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See http://forums.netbeans.org/viewtopic.php?t=21930&sid=2b46aea52793f04f323756e910a75300 Workaround is to explicitly add require 'myjar.jar' to the file.
Fixed in 8776e6b8f1bf. Note that with more than one jar in the classpath this still doesn't work with JRuby 1.4.0 due to http://jira.codehaus.org/browse/JRUBY-4265. It works when running since in that case the IDE can use the -classpath switch, but the debugger has to set the classpath through the CLASSPATH env variable.
Integrated into 'main-golden', will be available in build *201003240200* on http://bits.netbeans.org/dev/nightly/ (upload may still be in progress) Changeset: http://hg.netbeans.org/main/rev/8776e6b8f1bf User: Erno Mononen <emononen@netbeans.org> Log: #179364 - Classpath not set correctly when debugging