diff --git a/lib/vagrant/environment.rb b/lib/vagrant/environment.rb
index 021eb47ae..4541c7e7a 100644
--- a/lib/vagrant/environment.rb
+++ b/lib/vagrant/environment.rb
@@ -153,7 +153,7 @@ module Vagrant
     #
     # @return [String]
     def inspect
-      "#<#{self.class}: #{@cwd}>"
+      "#<#{self.class}: #{@cwd}>".encode('external')
     end
 
     # Action runner for executing actions in the context of this environment.
diff --git a/lib/vagrant/util/platform.rb b/lib/vagrant/util/platform.rb
index 37a5144c0..d2b399616 100644
--- a/lib/vagrant/util/platform.rb
+++ b/lib/vagrant/util/platform.rb
@@ -124,7 +124,7 @@ module Vagrant
             # Traverse each part and join it into the resulting path
             original.each do |single|
               Dir.entries(path).each do |entry|
-                if entry.downcase == single.downcase
+                if entry.downcase == single.encode('filesystem').downcase
                   path = path.join(entry)
                 end
               end