diff --git a/lib/vagrant/action/builtin.rb b/lib/vagrant/action/builtin.rb
index cd7600980..8377d293b 100644
--- a/lib/vagrant/action/builtin.rb
+++ b/lib/vagrant/action/builtin.rb
@@ -15,6 +15,7 @@ module Vagrant
       # start - Starts a VM, assuming it already exists on the
       # environment.
       start = Builder.new do
+        use VM::CleanMachineFolder
         use VM::Customize
         use VM::ClearForwardedPorts
         use VM::ForwardPorts
@@ -75,6 +76,7 @@ module Vagrant
         use VM::ClearNFSExports
         use VM::DestroyUnusedNetworkInterfaces
         use VM::Destroy
+        use VM::CleanMachineFolder
       end
 
       register :destroy, destroy
diff --git a/lib/vagrant/action/vm/clean_machine_folder.rb b/lib/vagrant/action/vm/clean_machine_folder.rb
new file mode 100644
index 000000000..6f8172f73
--- /dev/null
+++ b/lib/vagrant/action/vm/clean_machine_folder.rb
@@ -0,0 +1,37 @@
+require 'fileutils'
+
+module Vagrant
+  class Action
+    module VM
+      # Cleans up the VirtualBox machine folder for any ".xml-prev"
+      # files which VirtualBox may have left over. This is a bug in
+      # VirtualBox. As soon as this is fixed, this middleware can and
+      # will be removed.
+      class CleanMachineFolder
+        def initialize(app, env)
+          @app = app
+        end
+
+        def call(env)
+          clean_machine_folder
+          @app.call(env)
+        end
+
+        def clean_machine_folder
+          folder = File.join(VirtualBox::Global.global.system_properties.default_machine_folder, "*")
+          Dir[folder].each do |f|
+            next unless File.directory?(f)
+
+            keep = Dir["#{f}/**/*"].find do |d|
+              # Find a file that doesn't have ".xml-prev" as the suffix,
+              # which signals that we want to keep this folder
+              File.file?(d) && !(File.basename(d) =~ /\.xml-prev$/)
+            end
+
+            FileUtils.rm_rf(f) if !keep
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/test/vagrant/action/vm/clean_machine_folder_test.rb b/test/vagrant/action/vm/clean_machine_folder_test.rb
new file mode 100644
index 000000000..90b1ef06c
--- /dev/null
+++ b/test/vagrant/action/vm/clean_machine_folder_test.rb
@@ -0,0 +1,77 @@
+require File.join(File.dirname(__FILE__), '..', '..', '..', 'test_helper')
+
+class CleanMachineFolderVMActionTest < Test::Unit::TestCase
+  setup do
+    @klass = Vagrant::Action::VM::CleanMachineFolder
+    @app, @env = mock_action_data
+
+    @instance = @klass.new(@app, @env)
+  end
+
+  context "calling" do
+    should "clean machine folder then continue chain" do
+      seq = sequence("seq")
+      @instance.expects(:clean_machine_folder).in_sequence(seq)
+      @app.expects(:call).with(@env).in_sequence(seq)
+      @instance.call(@env)
+    end
+  end
+
+  context "cleaning the folder" do
+    setup do
+      @machine_folder = "foo"
+      @folder = File.join(@machine_folder, "*")
+      VirtualBox::Global.global.system_properties.stubs(:default_machine_folder).returns(@machine_folder)
+      File.stubs(:file?).returns(true)
+    end
+
+    should "ignore all non-directories" do
+      folders = %W[foo bar baz]
+      Dir.expects(:[]).with(@folder).returns(folders)
+      folders.each do |f|
+        File.expects(:directory?).with(f).returns(false)
+      end
+
+      FileUtils.expects(:rm_rf).never
+
+      @instance.clean_machine_folder
+    end
+
+    should "delete directories with only .xml-prev files" do
+      folders = {
+        "sfoo" => %W[foo bar baz.xml-prev],
+        "sbar" => %W[foo.xml-prev]
+      }
+
+      Dir.expects(:[]).with(@folder).returns(folders.keys)
+      folders.each do |folder, subfolders|
+        File.expects(:directory?).with(folder).returns(true)
+        Dir.expects(:[]).with("#{folder}/**/*").returns(subfolders)
+      end
+
+      FileUtils.expects(:rm_rf).never
+      FileUtils.expects(:rm_rf).with("sbar").once
+      @instance.clean_machine_folder
+    end
+
+    should "delete directories with only subdirectories" do
+      folders = {
+        "sfoo" => %W[foo bar],
+        "sbar" => %W[foo.xml-prev]
+      }
+
+      File.stubs(:file?).returns(false)
+      Dir.expects(:[]).with(@folder).returns(folders.keys)
+      folders.each do |folder, subfolders|
+        File.expects(:directory?).with(folder).returns(true)
+        Dir.expects(:[]).with("#{folder}/**/*").returns(subfolders)
+      end
+
+      FileUtils.expects(:rm_rf).never
+      FileUtils.expects(:rm_rf).with("sfoo").once
+      FileUtils.expects(:rm_rf).with("sbar").once
+
+      @instance.clean_machine_folder
+    end
+  end
+end
diff --git a/vagrant.gemspec b/vagrant.gemspec
index 69be899d4..fd444575e 100644
--- a/vagrant.gemspec
+++ b/vagrant.gemspec
@@ -9,7 +9,7 @@ Gem::Specification.new do |s|
 
   s.required_rubygems_version = Gem::Requirement.new("> 1.3.1") if s.respond_to? :required_rubygems_version=
   s.authors = ["Mitchell Hashimoto", "John Bender"]
-  s.date = %q{2010-07-13}
+  s.date = %q{2010-07-14}
   s.default_executable = %q{vagrant}
   s.description = %q{Vagrant is a tool for building and distributing virtualized development environments.}
   s.email = ["mitchell.hashimoto@gmail.com", "john.m.bender@gmail.com"]
@@ -47,6 +47,7 @@ Gem::Specification.new do |s|
      "lib/vagrant/action/exception_catcher.rb",
      "lib/vagrant/action/vm/boot.rb",
      "lib/vagrant/action/vm/check_guest_additions.rb",
+     "lib/vagrant/action/vm/clean_machine_folder.rb",
      "lib/vagrant/action/vm/clear_forwarded_ports.rb",
      "lib/vagrant/action/vm/clear_nfs_exports.rb",
      "lib/vagrant/action/vm/clear_shared_folders.rb",
@@ -134,6 +135,7 @@ Gem::Specification.new do |s|
      "test/vagrant/action/exception_catcher_test.rb",
      "test/vagrant/action/vm/boot_test.rb",
      "test/vagrant/action/vm/check_guest_additions_test.rb",
+     "test/vagrant/action/vm/clean_machine_folder_test.rb",
      "test/vagrant/action/vm/clear_forwarded_ports_test.rb",
      "test/vagrant/action/vm/clear_nfs_exports_test.rb",
      "test/vagrant/action/vm/clear_shared_folders_test.rb",
@@ -218,6 +220,7 @@ Gem::Specification.new do |s|
      "test/vagrant/action/exception_catcher_test.rb",
      "test/vagrant/action/vm/boot_test.rb",
      "test/vagrant/action/vm/check_guest_additions_test.rb",
+     "test/vagrant/action/vm/clean_machine_folder_test.rb",
      "test/vagrant/action/vm/clear_forwarded_ports_test.rb",
      "test/vagrant/action/vm/clear_nfs_exports_test.rb",
      "test/vagrant/action/vm/clear_shared_folders_test.rb",