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One of the pain points in having IronRuby access SharePoint classes is that you'll have to help IronRuby find the appropriate assemblies. IronRuby (at least with the 0.9.0 version) has an IronRuby folder underneath the lib folder in its main directory tree which you can populate with a "shortcut"...
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Yesterday I was banging my head against a (virtual) wall because of frustration trying to debug a WF -based workflow for SharePoint when I thought of a cool idea: why not use IronRuby and its REPL console to explore the SharePoint object model ? That would be cool and it would eliminate the need for...