diff --git a/lib/hobo.rb b/lib/hobo.rb
index c5d135310..3b83ce490 100644
--- a/lib/hobo.rb
+++ b/lib/hobo.rb
@@ -2,8 +2,8 @@ libdir = File.dirname(__FILE__)
 $:.unshift(libdir)
 PROJECT_ROOT = File.join(libdir, '..')
 
-require 'ostruct'
 require 'ftools'
+require 'pathname'
 require 'logger'
 require 'virtualbox'
 require 'hobo/config'
diff --git a/lib/hobo/env.rb b/lib/hobo/env.rb
index 85eeddeff..af44cb5bc 100644
--- a/lib/hobo/env.rb
+++ b/lib/hobo/env.rb
@@ -8,7 +8,7 @@ module Hobo
       :files => CONFIG.merge({}), #additional files go mhia!
       :dirs => [HOME] #additional dirs go mhia!
     }
-    PATH_CHUNK_REGEX = /\/[^\/]+$/
+
 
     class << self
       def load!
@@ -41,16 +41,16 @@ module Hobo
         @@persisted_uuid = load_dotfile
       end
 
-      def load_dotfile(dir=Dir.pwd)
-        return nil if dir.empty?
+      def load_dotfile(path=Pathname.new(Dir.pwd))
+        return nil if path.to_s == '/'
 
-        file = "#{dir}/#{Hobo.config[:dotfile_name]}"
+        file = "#{path}/#{Hobo.config[:dotfile_name]}"
         if File.exists?(file)
           # TODO check multiple lines after the first for information
           return File.open(file, 'r').first
         end
         
-        load_dotfile(dir.sub(PATH_CHUNK_REGEX, '')) 
+        load_dotfile(path.parent)
       end
 
       def persisted_uuid
diff --git a/test/hobo/env_test.rb b/test/hobo/env_test.rb
index 02e23230f..df4b8014c 100644
--- a/test/hobo/env_test.rb
+++ b/test/hobo/env_test.rb
@@ -73,9 +73,10 @@ class EnvTest < Test::Unit::TestCase
     
     test "should walk the parent directories looking for the dotfile" do
       Hobo.config! hobo_mock_config
+
       #Expects exists with the current directory and .hobo 
       File.expects(:exists?).with(dotfile).returns(false)
-      File.expects(:exists?).with(dotfile(Dir.pwd.sub(Hobo::Env::PATH_CHUNK_REGEX, ''))).returns(true)
+      File.expects(:exists?).with(dotfile(Dir.pwd.split('/')[0..-2].join('/'))).returns(true)
       File.expects(:open).returns(['foo'])
       Hobo::Env.load_uuid!
       assert_equal Hobo::Env.persisted_uuid, 'foo'