diff --git a/lib/vagrant/config.rb b/lib/vagrant/config.rb
index f939bd0ec..4b0cc93b1 100644
--- a/lib/vagrant/config.rb
+++ b/lib/vagrant/config.rb
@@ -25,6 +25,7 @@ module Vagrant
     # current version is always considered to be the last version in this
     # list.
     VERSIONS_ORDER = ["1"]
+    CURRENT_VERSION = VERSIONS_ORDER.last
 
     # This is the method which is called by all Vagrantfiles to configure Vagrant.
     # This method expects a block which accepts a single argument representing
diff --git a/lib/vagrant/config/v1/loader.rb b/lib/vagrant/config/v1/loader.rb
index 45b9e0ba3..910ae3dda 100644
--- a/lib/vagrant/config/v1/loader.rb
+++ b/lib/vagrant/config/v1/loader.rb
@@ -84,10 +84,16 @@ module Vagrant
         protected
 
         def self.new_root_object
-          # Get all the registered configuration objects and use them.
-          config_map = {}
-          Vagrant.plugin("1").manager.config.each do |key, klass|
-            config_map[key] = klass
+          # Get all the registered configuration objects and use them. If
+          # we're currently on version 1, then we load all the config objects,
+          # otherwise we load only the upgrade safe ones, since we're
+          # obviously being loaded for an upgrade.
+          config_map = nil
+          plugin_manager = Vagrant.plugin("1").manager
+          if Config::CURRENT_VERSION == "1"
+            config_map = plugin_manager.config
+          else
+            config_map = plugin_manager.config_upgrade_safe
           end
 
           # Create the configuration root object
diff --git a/test/unit/vagrant/config/v1/loader_test.rb b/test/unit/vagrant/config/v1/loader_test.rb
index a8dd85a47..e296a4972 100644
--- a/test/unit/vagrant/config/v1/loader_test.rb
+++ b/test/unit/vagrant/config/v1/loader_test.rb
@@ -1,3 +1,5 @@
+require "ostruct"
+
 require File.expand_path("../../../../base", __FILE__)
 
 describe Vagrant::Config::V1::Loader do
@@ -8,12 +10,44 @@ describe Vagrant::Config::V1::Loader do
       result = described_class.init
       result.should be_kind_of(Vagrant::Config::V1::Root)
     end
+
+    it "returns an object with all configuration keys loaded if V1" do
+      # Make sure we're version 1
+      stub_const("Vagrant::Config::CURRENT_VERSION", "1")
+
+      # Register some config classes.
+      register_plugin do |p|
+        p.config("foo") { OpenStruct }
+        p.config("bar", true) { OpenStruct }
+      end
+
+      # Test that we have all keys
+      result = described_class.init
+      result.foo.should be_kind_of(OpenStruct)
+      result.bar.should be_kind_of(OpenStruct)
+    end
+
+    it "returns only upgradable config objects if not V1" do
+      # Make sure we're NOT version 1
+      stub_const("Vagrant::Config::CURRENT_VERSION", "2")
+
+      # Register some config classes.
+      register_plugin do |p|
+        p.config("foo") { OpenStruct }
+        p.config("bar", true) { OpenStruct }
+      end
+
+      # Test that we have all keys
+      result = described_class.init
+      result.bar.should be_kind_of(OpenStruct)
+      expect { result.foo }.to raise_error(NoMethodError)
+    end
   end
 
   describe "finalizing" do
     it "should call `#finalize` on the configuration object" do
       # Register a plugin for our test
-      plugin_class = register_plugin do |plugin|
+      register_plugin do |plugin|
         plugin.name "test"
         plugin.config "foo" do
           Class.new do
@@ -44,13 +78,8 @@ describe Vagrant::Config::V1::Loader do
   describe "loading" do
     it "should configure with all plugin config keys loaded" do
       # Register a plugin for our test
-      plugin_class = register_plugin do |plugin|
-        plugin.name "test"
-        plugin.config "foo" do
-          Class.new do
-            attr_accessor :bar
-          end
-        end
+      register_plugin do |plugin|
+        plugin.config("foo") { OpenStruct }
       end
 
       # Create the proc we're testing
diff --git a/vagrant.gemspec b/vagrant.gemspec
index 661d9b69b..1f419593a 100644
--- a/vagrant.gemspec
+++ b/vagrant.gemspec
@@ -28,9 +28,9 @@ Gem::Specification.new do |s|
   s.add_development_dependency "minitest", "~> 2.5.1"
   s.add_development_dependency "mocha"
   #s.add_development_dependency "sys-proctable", "~> 0.9.0"
-  s.add_development_dependency "rspec-core", "~> 2.8.0"
-  s.add_development_dependency "rspec-expectations", "~> 2.8.0"
-  s.add_development_dependency "rspec-mocks", "~> 2.8.0"
+  s.add_development_dependency "rspec-core", "~> 2.11.0"
+  s.add_development_dependency "rspec-expectations", "~> 2.11.0"
+  s.add_development_dependency "rspec-mocks", "~> 2.11.0"
 
   s.files         = `git ls-files`.split("\n")
   s.executables   = `git ls-files`.split("\n").map{|f| f[/^bin\/(.*)/, 1]}.compact