This topic might be a little bit old, but since I run into this issue 
recently here's the solution:

Due to a lack of multipart form support for integration tests in Action 
Pack Webrat's attach_file does not work with Rails 2.0.2.

I posted a workaround on our blog: 
http://devblog.imedo.de/2009/9/2/file-uploads-with-webrat-in-ruby-on-rails-2-0-2.
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