diff --git a/CHANGELOG.md b/CHANGELOG.md
index 09a9220f4..42574ff8a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,7 @@
   - Arbitrary options to puppet binary can be set with `config.puppet.options`. [GH-242]
   - BSD hosts use proper GNU sed syntax for clearing NFS shares. [GH-243]
   - Enumerate VMs in a multi-VM environment in order they were defined. [GH-244]
+  - Check for VM boot changed to use `timeout` library, which works better with Windows.
 
 ## 0.6.8 (November 30, 2010)
 
diff --git a/lib/vagrant/ssh.rb b/lib/vagrant/ssh.rb
index 987d20e3d..38f1424de 100644
--- a/lib/vagrant/ssh.rb
+++ b/lib/vagrant/ssh.rb
@@ -1,3 +1,4 @@
+require 'timeout'
 require 'net/ssh'
 require 'net/scp'
 require 'mario'
@@ -92,21 +93,16 @@ module Vagrant
     #
     # @return [Boolean]
     def up?
-      check_thread = Thread.new do
-        begin
-          Thread.current[:result] = false
-          execute(:timeout => env.config.ssh.timeout) do |ssh|
-            Thread.current[:result] = true
-          end
-        rescue Errno::ECONNREFUSED, Net::SSH::Disconnect, Errors::SSHConnectionRefused
-          # False, its defaulted above
-        end
+      Timeout.timeout(env.config.ssh.timeout) do
+        execute(:timeout => env.config.ssh.timeout) { |ssh| }
       end
 
-      check_thread.join(env.config.ssh.timeout)
-      return check_thread[:result]
+      true
     rescue Net::SSH::AuthenticationFailed
       raise Errors::SSHAuthenticationFailed.new
+    rescue Timeout::Error, Errno::ECONNREFUSED, Net::SSH::Disconnect,
+           Errors::SSHConnectionRefused, Net::SSH::AuthenticationFailed
+      return false
     end
 
     # Checks the file permissions for the private key, resetting them
diff --git a/test/vagrant/ssh_test.rb b/test/vagrant/ssh_test.rb
index 6aa970dd0..93542c5f9 100644
--- a/test/vagrant/ssh_test.rb
+++ b/test/vagrant/ssh_test.rb
@@ -195,16 +195,15 @@ class SshTest < Test::Unit::TestCase
     end
 
     should "return false if SSH connection times out" do
-      Net::SSH.expects(:start)
-      assert !@ssh.up?
-    end
+      @env.config.ssh.timeout = 0.5
 
-    should "allow the thread the configured timeout time" do
-      @thread = mock("thread")
-      @thread.stubs(:[])
-      Thread.expects(:new).returns(@thread)
-      @thread.expects(:join).with(@env.config.ssh.timeout).once
-      @ssh.up?
+      Net::SSH.stubs(:start).with() do
+        # Sleep here to artificially fake timeout
+        sleep 1
+        true
+      end
+
+      assert !@ssh.up?
     end
 
     should "return false if the connection is refused" do