I've been trying (without success) to install the plugin vagrant-digitalocean in a Windows environment. I installed the latest version of Vagrant (1.3.1) However, when I try and install the plugin for digitalocean, the install fails: $ vagrant plugin install vagrant-digitalocean Installing the 'vagrant-digitalocean' plugin. This can take a few minutes... C:/Tools2/Vagrant/embedded/lib/ruby/site_ruby/1.9.1/rubygems/installer.rb:556:in `rescue in block in build_extensions': ERROR: Failed to build gem native extension. (Gem::Installer::ExtensionBuildError) C:/Tools2/Vagrant/embedded/bin/ruby.exe extconf.rb creating Makefile make generating generator-i386-mingw32.def compiling generator.c linking shared-object json/ext/generator.so make install /usr/bin/install -c -m 0755 generator.so C: /usr/bin/install -c -m 0755 generator.so . /usr/bin/install: `generator.so' and `./generator.so' are the same file make: *** [and] Error 1 Unfortunately I'm too new to Vagrant / DigialOcean to know where the problem lies. (I don't seem to have any problem building the json gem in a pure ruby+devkit environment. Having spent a few hours on this without any success, I'm about to abandon hope! Does anyone have a working installation? Does anybody recognize a common problem? Thanks.