diff --git a/lib/vagrant/action/builder.rb b/lib/vagrant/action/builder.rb
index 526dfe8b2..c828c1eb6 100644
--- a/lib/vagrant/action/builder.rb
+++ b/lib/vagrant/action/builder.rb
@@ -50,12 +50,19 @@ module Vagrant
       # @param [Vagrant::Action::Environment] env The action environment
       # @return [Object] A callable object
       def to_app(env)
-        items = stack.collect do |item|
+        # Prepend the error halt task so errneous environments are halted
+        # before the chain even begins.
+        items = stack.dup.unshift([ErrorHalt, [], nil])
+
+        # Convert each middleware into a lambda which takes the next
+        # middleware.
+        items = items.collect do |item|
           klass, args, block = item
           lambda { |app| klass.new(app, env, *args, &block) }
         end
 
-        items << lambda { |env| } # The final step, which simply returns
+        # Append the final step and convert into flattened call chain.
+        items << lambda { |env| }
         items[0...-1].reverse.inject(items.last) { |a,e| e.call(a) }
       end
 
diff --git a/lib/vagrant/action/error_halt.rb b/lib/vagrant/action/error_halt.rb
new file mode 100644
index 000000000..2c4411659
--- /dev/null
+++ b/lib/vagrant/action/error_halt.rb
@@ -0,0 +1,14 @@
+module Vagrant
+  class Action
+    # A middleware which simply halts if the environment is erroneous.
+    class ErrorHalt
+      def initialize(app,env)
+        @app = app
+      end
+
+      def call(env)
+        @app.call(env) if !env.error?
+      end
+    end
+  end
+end
diff --git a/test/vagrant/action/builder_test.rb b/test/vagrant/action/builder_test.rb
index 1254fbda6..2b8aa372f 100644
--- a/test/vagrant/action/builder_test.rb
+++ b/test/vagrant/action/builder_test.rb
@@ -47,16 +47,17 @@ class ActionBuilderTest < Test::Unit::TestCase
     end
 
     context "converting to an app" do
-      should "initialize each middleware with app and env" do
-        # TODO: better testing of this method... somehow
-
+      should "preprend error halt to the chain" do
         result = mock("result")
         env = {:a => :b}
         middleware = mock("middleware")
         middleware.expects(:new).with(anything, env).returns(result)
         @instance.use middleware
-        assert_equal result, @instance.to_app(env)
+        result = @instance.to_app(env)
+        assert result.kind_of?(Vagrant::Action::ErrorHalt)
       end
+
+      # TODO: Better testing of this method
     end
 
     context "calling" do
@@ -79,8 +80,11 @@ class ActionBuilderTest < Test::Unit::TestCase
           true
         end
 
+        env = Vagrant::Action::Environment.new(nil)
+        env[:key] = :value
+
         @instance.use(mw)
-        @instance.call(:key => :value)
+        @instance.call(env)
       end
     end
   end
diff --git a/test/vagrant/action/error_halt_test.rb b/test/vagrant/action/error_halt_test.rb
new file mode 100644
index 000000000..4f3af8771
--- /dev/null
+++ b/test/vagrant/action/error_halt_test.rb
@@ -0,0 +1,21 @@
+require File.join(File.dirname(__FILE__), '..', '..', 'test_helper')
+
+class ErrorHaltTest < Test::Unit::TestCase
+  setup do
+    @klass = Vagrant::Action::ErrorHalt
+    @app, @env = mock_action_data
+    @instance = @klass.new(@app, @env)
+  end
+
+  should "continue the chain if no error" do
+    assert !@env.error?
+    @app.expects(:call).with(@env).once
+    @instance.call(@env)
+  end
+
+  should "halt the chain if an error occured" do
+    @env.error!(:foo)
+    @app.expects(:call).never
+    @instance.call(@env)
+  end
+end