diff --git a/middleman-core/lib/middleman-core/core_extensions/request.rb b/middleman-core/lib/middleman-core/core_extensions/request.rb
index cb706668..33eabf7f 100644
--- a/middleman-core/lib/middleman-core/core_extensions/request.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/request.rb
@@ -146,7 +146,7 @@ module Middleman
           opts[:app] = app_class
 
           require "webrick"
-          opts[:Logger] = WEBrick::Log::new("/dev/null", 7) if !options[:logging]
+          opts[:Logger] = WEBrick::Log::new(RUBY_PLATFORM =~ /(mingw|bccwin|wince|mswin32)/i ? 'NUL:' : '/dev/null', 7) if !options[:logging]
           opts[:server] = 'webrick'
 
           server = ::Rack::Server.new(opts)
@@ -370,4 +370,4 @@ module Middleman
       end
     end
   end
-end
\ No newline at end of file
+end