diff --git a/lib/hobo/env.rb b/lib/hobo/env.rb
index af44cb5bc..924adf8ee 100644
--- a/lib/hobo/env.rb
+++ b/lib/hobo/env.rb
@@ -2,16 +2,24 @@ require 'yaml'
 
 module Hobo
   class Env
+    HOBOFILE_NAME = "hobofile"
     HOME =  File.expand_path('~/.hobo')
     CONFIG = { File.join(HOME, 'config.yml') => '/config/default.yml' }
-    ENSURE = { 
+    ENSURE = {
       :files => CONFIG.merge({}), #additional files go mhia!
       :dirs => [HOME] #additional dirs go mhia!
     }
 
+    # Initialize class variables used
+    @@persisted_uuid = nil
+    @@root_path = nil
 
     class << self
+      def persisted_uuid; @@persisted_uuid; end
+      def root_path; @@root_path; end
+
       def load!
+        load_root_path!
         load_config!
         load_uuid!
       end
@@ -27,34 +35,42 @@ module Hobo
           File.copy(File.join(PROJECT_ROOT, default), target) unless File.exists?(target)
         end
       end
-      
+
       def load_config!
         ensure_directories
         ensure_files
-        
+
         HOBO_LOGGER.info "Loading config from #{CONFIG.keys.first}"
         parsed = YAML.load_file(CONFIG.keys.first)
         Hobo.config!(parsed)
       end
 
       def load_uuid!
-        @@persisted_uuid = load_dotfile
-      end
-
-      def load_dotfile(path=Pathname.new(Dir.pwd))
-        return nil if path.to_s == '/'
-
-        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
+        File.open(File.join(root_path, Hobo.config[:dotfile_name])) do |f|
+          @@persisted_uuid = f.read
         end
-        
-        load_dotfile(path.parent)
+      rescue Errno::ENOENT
+        @@persisted_uuid = nil
       end
 
-      def persisted_uuid
-        @@persisted_uuid
+      def load_root_path!(path=Pathname.new(Dir.pwd))
+        if path.to_s == '/'
+          error_and_exit("UH OH")
+          return
+        end
+
+        file = "#{path}/#{HOBOFILE_NAME}"
+        if File.exist?(file)
+          @@root_path = path.to_s
+          return
+        end
+
+        load_root_path!(path.parent)
+      end
+
+      def error_and_exit(error)
+        puts error
+        exit
       end
     end
   end
diff --git a/test/hobo/env_test.rb b/test/hobo/env_test.rb
index df4b8014c..3007c7a46 100644
--- a/test/hobo/env_test.rb
+++ b/test/hobo/env_test.rb
@@ -1,13 +1,39 @@
 require File.join(File.dirname(__FILE__), '..', 'test_helper')
 
 class EnvTest < Test::Unit::TestCase
-  context "Hobo environment handler" do
+  def dot_file_expectation
+    File.expects(:exists?).at_least_once.returns(true)
+    File.expects(:open).with(dotfile, 'r').returns(['foo'])
+  end
+
+  def config_file_expectation
+    YAML.expects(:load_file).with(Hobo::Env::CONFIG.keys.first).returns(hobo_mock_config)
+  end
+
+  def dotfile(dir=Dir.pwd)
+    "#{dir}/#{hobo_mock_config[:dotfile_name]}"
+  end
+
+  setup do
+    Hobo::Env.stubs(:error_and_exit)
+  end
+
+  context "initial load" do
+    test "load! should load the config and set the persisted_uid" do
+      Hobo::Env.expects(:load_config!).once
+      Hobo::Env.expects(:load_uuid!).once
+      Hobo::Env.expects(:load_root_path!).once
+      Hobo::Env.load!
+    end
+  end
+
+  context "loading config" do
     setup do
       @handler = Hobo::Env
       @ensure = Hobo::Env::ENSURE
       Hobo.config! nil
     end
-    
+
     test "should not create any directories if they exist"  do
       File.expects(:exists?).times(@ensure[:dirs].length).returns(true)
       Dir.expects(:mkdir).never
@@ -19,80 +45,87 @@ class EnvTest < Test::Unit::TestCase
       File.expects(:copy).never
       @handler.ensure_files
     end
-    
+
     test "should create the ensured directories if they don't exist" do
       file_seq = sequence("file_seq")
-      
+
       @ensure[:dirs].each do |dir|
         File.expects(:exists?).returns(false).in_sequence(file_seq)
         Dir.expects(:mkdir).with(dir).in_sequence(file_seq)
       end
-      
+
       @handler.ensure_directories
     end
-    
+
     test "should create the ensured files if they don't exist" do
       file_seq = sequence("file_seq")
-      
+
       @ensure[:files].each do |target, default|
         File.expects(:exists?).with(target).returns(false).in_sequence(file_seq)
         File.expects(:copy).with(File.join(PROJECT_ROOT, default), target).in_sequence(file_seq)
       end
-      
+
       @handler.ensure_files
     end
 
     test "should load of the default" do
       config_file_expectation
       @handler.load_config!
-      assert_equal Hobo.config[:ssh], hobo_mock_config[:ssh]                                    
+      assert_equal Hobo.config[:ssh], hobo_mock_config[:ssh]
     end
 
     test "Hobo.config should be nil unless loaded" do
       assert_equal Hobo.config, nil
     end
+  end
 
+  context "loading the UUID out from the persisted file" do
     test "loading of the uuid from the dotfile" do
-      dot_file_expectation
       Hobo.config! hobo_mock_config
+
+      filemock = mock("filemock")
+      filemock.expects(:read).returns("foo")
+      File.expects(:open).with(File.join(Hobo::Env.root_path, hobo_mock_config[:dotfile_name])).once.yields(filemock)
       Hobo::Env.load_uuid!
       assert_equal Hobo::Env.persisted_uuid, 'foo'
     end
 
-    test "load! should load the config and set the persisted_uid" do
-      config_file_expectation
-      dot_file_expectation
-      Hobo::Env.load!
-    end
-
-    test "when no dotfile exists uuid should be nil" do
-      Hobo.config! hobo_mock_config.merge(:dotfile_name => 'unpossiblyunpossiblfilename')
+    test "uuid should be nil if dotfile didn't exist" do
+      File.expects(:open).raises(Errno::ENOENT)
       Hobo::Env.load_uuid!
-      assert_equal Hobo::Env.persisted_uuid, nil
+      assert_nil Hobo::Env.persisted_uuid
     end
-    
-    test "should walk the parent directories looking for the dotfile" do
-      Hobo.config! hobo_mock_config
+  end
 
-      #Expects exists with the current directory and .hobo 
-      File.expects(:exists?).with(dotfile).returns(false)
-      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'
+  context "loading the root path" do
+    test "should walk the parent directories looking for hobofile" do
+      paths = [
+        Pathname.new("/foo/bar/baz"),
+        Pathname.new("/foo/bar"),
+        Pathname.new("/foo")
+      ]
+
+      search_seq = sequence("search_seq")
+      paths.each do |path|
+        File.expects(:exist?).with("#{path}/#{Hobo::Env::HOBOFILE_NAME}").returns(false).in_sequence(search_seq)
+      end
+
+      assert_nil Hobo::Env.load_root_path!(paths.first)
     end
 
-    def dot_file_expectation
-      File.expects(:exists?).at_least_once.returns(true)
-      File.expects(:open).with(dotfile, 'r').returns(['foo'])
+    test "should print out an error and exit if not found" do
+      path = Pathname.new("/")
+
+      Hobo::Env.expects(:error_and_exit).once
+      Hobo::Env.load_root_path!(path)
     end
 
-    def config_file_expectation
-      YAML.expects(:load_file).with(Hobo::Env::CONFIG.keys.first).returns(hobo_mock_config)
-    end
+    test "should set the path for the Hobofile" do
+      path = "/foo"
+      File.expects(:exist?).with("#{path}/#{Hobo::Env::HOBOFILE_NAME}").returns(true)
+      Hobo::Env.load_root_path!(Pathname.new(path))
 
-    def dotfile(dir=Dir.pwd)
-      "#{dir}/#{hobo_mock_config[:dotfile_name]}"
+      assert_equal path, Hobo::Env.root_path
     end
   end
 end