diff --git a/lib/vagrant/environment.rb b/lib/vagrant/environment.rb
index dacdaa579..2423e8d44 100644
--- a/lib/vagrant/environment.rb
+++ b/lib/vagrant/environment.rb
@@ -598,9 +598,8 @@ module Vagrant
     #
     # @return [Pathname]
     def setup_home_path
-      @home_path = Pathname.new(File.expand_path(@home_path ||
-                                                 ENV["VAGRANT_HOME"] ||
-                                                 Vagrant.user_data_path))
+      @home_path = Util::Platform.fs_real_path(
+        @home_path || ENV["VAGRANT_HOME"] || Vagrant.user_data_path)
       @logger.info("Home path: #{@home_path}")
 
       # Setup the list of child directories that need to be created if they
diff --git a/lib/vagrant/util/platform.rb b/lib/vagrant/util/platform.rb
index 120db6986..489ef63ff 100644
--- a/lib/vagrant/util/platform.rb
+++ b/lib/vagrant/util/platform.rb
@@ -61,6 +61,24 @@ module Vagrant
         def fs_real_path(path)
           path = Pathname.new(File.expand_path(path))
 
+          if path.exist? && !fs_case_sensitive?
+            # Build up all the parts of the path
+            original = []
+            while !path.root?
+              original.unshift(path.basename.to_s)
+              path = path.parent
+            end
+
+            # 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
+                  path = path.join(entry)
+                end
+              end
+            end
+          end
+
           if windows?
             # Fix the drive letter to be uppercase.
             path = path.to_s
@@ -71,25 +89,6 @@ module Vagrant
             path = Pathname.new(path)
           end
 
-          return path if !path.exist?
-          return path if fs_case_sensitive?
-
-          # Build up all the parts of the path
-          original = []
-          while !path.root?
-            original.unshift(path.basename.to_s)
-            path = path.parent
-          end
-
-          # 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
-                path = path.join(entry)
-              end
-            end
-          end
-
           path
         end
 
diff --git a/test/unit/vagrant/environment_test.rb b/test/unit/vagrant/environment_test.rb
index b3c863d93..d686c09ce 100644
--- a/test/unit/vagrant/environment_test.rb
+++ b/test/unit/vagrant/environment_test.rb
@@ -230,19 +230,15 @@ describe Vagrant::Environment do
     end
 
     context "default home path" do
-      before :each do
-        Vagrant::Util::Platform.stub(:windows? => false)
-      end
-
       it "is set to '~/.vagrant.d' by default" do
-        expected = Pathname.new(File.expand_path("~/.vagrant.d"))
+        expected = Vagrant::Util::Platform.fs_real_path("~/.vagrant.d")
         described_class.new.home_path.should == expected
       end
 
       it "is set to '~/.vagrant.d' if on Windows but no USERPROFILE" do
         Vagrant::Util::Platform.stub(:windows? => true)
 
-        expected = Pathname.new(File.expand_path("~/.vagrant.d"))
+        expected = Vagrant::Util::Platform.fs_real_path("~/.vagrant.d")
 
         with_temp_env("USERPROFILE" => nil) do
           described_class.new.home_path.should == expected
@@ -253,7 +249,7 @@ describe Vagrant::Environment do
         Vagrant::Util::Platform.stub(:windows? => true)
 
         Dir.mktmpdir do |dir|
-          expected = Pathname.new(File.expand_path("#{dir}/.vagrant.d"))
+          expected = Vagrant::Util::Platform.fs_real_path("#{dir}/.vagrant.d")
 
           with_temp_env("USERPROFILE" => dir) do
             described_class.new.home_path.should == expected