You need to install a bunch of gems locally since the remote installation didn’t work or at least not stably.
By assumption that InstantRails2.0 is ready on your XP platform, then you could go on the following steps:
1 download NetBeans6.8, which is a wonderful IDE for Ruby world, download it freely here:
http://netbeans.org/downloads/index.html
remember download the ruby one, which is around 92M.
2 download all related gems for debugging ruby. Here is the list(please Google them by names):
2010-03-25 09:17 15,360 columnize-0.3.0.gem
2010-03-25 09:10 31,744 linecache-0.43-mswin32.gem
2010-03-24 17:27 117,760 ruby-debug-0.10.3.gem
2010-03-25 09:11 113,152 ruby-debug-base-0.10.3-mswin32.gem
2010-03-24 16:20 36,864 ruby-debug-base-0.9.2-mswin32.gem
2009-12-09 16:16 31,744 ruby-debug-ide-0.4.6.gem
The order of installation is columnize->linecache->ruby-debug-base->ruby-debug->ruby-debug-ide
3 launch NetBeans, new project with existing ruby project codes, for me, I import redmine project.
Note that the build-in ruby platform is JRuby-1.4.0, you get to change it to Ruby 1.8.6-p111 which should be installed under your InstantRails2.0/ruby.
Anyway, by clicking tools->ruby platform, if you see quick debug engine of ruby is (ruby-debug-ide)
Then ruby debug enviroment is ready for you, you could set breakpoints/step in/step out/run to cursor just as what you could do with java/c++ codes.
本文介绍如何在Windows XP平台上为Ruby项目设置本地调试环境。首先安装NetBeans 6.8作为集成开发环境,然后下载并安装一系列调试所需的gems,包括columnize、linecache等。最后通过NetBeans导入现有项目,并调整Ruby平台版本。

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