I\'m trying to do file uploads with ruby 1.8 and it seems like there are no good out-of-the-box solutions. They all seem to need some 3rd party patch or fork of a project to
Ultimately, in win7 with ruby 1.9.1 the following worked for me (where paths need to be updated to reflect the location (and version) of your curl version (which can be obtained via http://curl.haxx.se/download.html#Win32))
gem install curb -- --with-curl-lib="C:/curl/curl-7.21.1-devel-mingw32/bin" --with-curl-include="C:/curl/curl-7.21.1-devel-mingw32/include"
This did take a few minutes to process, so be patient.