Ruby sucks.

Rakefile

@@ -93,7 +93,7 @@ task 'dlls' do
   [ w64, w32 ].each do |opt|
     env_comp = "CC=#{opt[:cross]}-gcc "
     env_comp += "LD=#{opt[:cross]}-gcc "
-    docker_for_windows "#{env} #{env_comp} make -j #{out} && #{opt[:cross]}-strip -x -S #{out} && cp #{out} #{opt[:out]}"
+    docker_for_windows "gem update --system && #{env} #{env_comp} make -j #{out} && #{opt[:cross]}-strip -x -S #{out} && cp #{out} #{opt[:out]}"
   end
 
 end
@@ -110,7 +110,7 @@ task 'gem:native' do
     system "rake cross native gem RUBY_CC_VERSION=2.4.0:2.3.0:2.2.2:2.1.5:2.0.0 V=#{verbose} GRPC_CONFIG=#{grpc_config}"
   else
     Rake::Task['dlls'].execute
-    docker_for_windows "bundle && rake cross native gem RUBY_CC_VERSION=2.4.0:2.3.0:2.2.2:2.1.5:2.0.0 V=#{verbose} GRPC_CONFIG=#{grpc_config}"
+    docker_for_windows "gem update --system && bundle && rake cross native gem RUBY_CC_VERSION=2.4.0:2.3.0:2.2.2:2.1.5:2.0.0 V=#{verbose} GRPC_CONFIG=#{grpc_config}"
   end
 end