My guess is that the last time the vagrant package sucessfully built, was when Ruby 2.5 was available before Ruby 2.6 was there. Vagrant seems to be broken because its dependency rubygem-winrm-2_1 is broken. It seems that rubygem-winrm is broken because of a bug when generating the documentation: https://github.com/ruby/rdoc/issues/705 My suggestion is to package rubygem-winrm (not necessarily 2.1 as I expect vagrant to can build when the last version as well) WITHOUT documentation and use this version to build vagrant. This would be the only way without a fix for the bug in rdoc.