diff --git a/Rakefile b/Rakefile
index c4e0092b1..3853d3865 100644
--- a/Rakefile
+++ b/Rakefile
@@ -1,6 +1,7 @@
 require 'rubygems'
 require 'bundler/setup'
 require 'rake/testtask'
+require 'rspec/core/rake_task'
 Bundler::GemHelper.install_tasks
 
 task :default => "test:unit"
@@ -12,9 +13,8 @@ namespace :test do
     t.pattern = "test/unit/**/*_test.rb"
   end
 
-  Rake::TestTask.new do |t|
+  RSpec::Core::RakeTask.new do |t|
     t.name = "acceptance"
-    t.libs << "test/acceptance"
     t.pattern = "test/acceptance/**/*_test.rb"
   end
 end
diff --git a/test/acceptance/base.rb b/test/acceptance/base.rb
index bbb2bbbe2..bd97fd042 100644
--- a/test/acceptance/base.rb
+++ b/test/acceptance/base.rb
@@ -1,11 +1,11 @@
 require "rubygems"
-require "contest"
+require "rspec/autorun"
+
 require "log4r"
 
-require File.expand_path("../helpers/config", __FILE__)
-require File.expand_path("../helpers/isolated_environment", __FILE__)
-require File.expand_path("../helpers/output", __FILE__)
-require File.expand_path("../helpers/virtualbox", __FILE__)
+require File.expand_path("../support/base_context", __FILE__)
+require File.expand_path("../support/config", __FILE__)
+require File.expand_path("../support/virtualbox", __FILE__)
 
 # If VirtualBox is currently running, fail.
 if Acceptance::VirtualBox.find_vboxsvc
@@ -32,55 +32,7 @@ end
 
 $acceptance_options = Acceptance::Config.new(ENV["ACCEPTANCE_CONFIG"])
 
-class AcceptanceTest < Test::Unit::TestCase
-  # This method is a shortcut to give access to the global configuration
-  # setup by the acceptance tests.
-  def config
-    $acceptance_options
-  end
-
-  # Executes the given command in the isolated environment. This
-  # is just a shortcut to IsolatedEnvironment#execute.
-  #
-  # @return [Object]
-  def execute(*args, &block)
-    @environment.execute(*args, &block)
-  end
-
-  # This is a shortcut method to instantiate an Output matcher.
-  #
-  # @return [Acceptance::Output]
-  def output(text)
-    Acceptance::Output.new(text)
-  end
-
-  # This method is an assertion helper for asserting that a process
-  # succeeds. It is a wrapper around `execute` that asserts that the
-  # exit status was successful.
-  def assert_execute(*args, &block)
-    result = execute(*args, &block)
-    assert(result.success?, "expected '#{args.join(" ")}' to succeed")
-    result
-  end
-
-  setup do
-    # Wait for VBoxSVC to disappear
-    Acceptance::VirtualBox.wait_for_vboxsvc
-
-    # Setup the environment so that we have an isolated area
-    # to run Vagrant. We do some configuration here as well in order
-    # to replace "vagrant" with the proper path to Vagrant as well
-    # as tell the isolated environment about custom environmental
-    # variables to pass in.
-    apps = { "vagrant" => config.vagrant_path }
-    @environment = Acceptance::IsolatedEnvironment.new(apps, config.env)
-
-    # Setup a logger for this test, since tests often log to assist
-    # with the debugging process in case of failure.
-    @logger = Log4r::Logger.new("acceptance::#{self.class.name.downcase.gsub("test", "")}")
-  end
-
-  teardown do
-    @environment.close if @environment
-  end
+# Configure RSpec
+RSpec.configure do |c|
+  c.expect_with :stdlib
 end
diff --git a/test/acceptance/box_test.rb b/test/acceptance/box_test.rb
index 41bac64c4..d81115115 100644
--- a/test/acceptance/box_test.rb
+++ b/test/acceptance/box_test.rb
@@ -1,19 +1,21 @@
 require File.expand_path("../base", __FILE__)
 
-class BoxTest < AcceptanceTest
+describe "vagrant box" do
+  include_context "acceptance"
+
   def require_box(name)
     if !config.boxes.has_key?(name) || !File.file?(config.boxes[name])
       raise ArgumentError, "The configuration should specify a '#{name}' box."
     end
   end
 
-  should "have no boxes by default" do
+  it "has no boxes by default" do
     result = execute("vagrant", "box", "list")
     assert(output(result.stdout).no_boxes,
            "output should say there are no installed boxes")
   end
 
-  should "add a box from a file" do
+  it "can add a box from a file" do
     require_box("default")
 
     # Add the box, which we expect to succeed
@@ -26,15 +28,15 @@ class BoxTest < AcceptanceTest
            "foo box should exist after it is added")
   end
 
-  should "give an error if the file doesn't exist" do
+  it "gives an error if the file doesn't exist" do
     results = execute("vagrant", "box", "add", "foo", "/tmp/nope/nope/nope/nonono.box")
     assert(!results.success?, "Box add should fail.")
     assert(output(results.stdout).box_path_doesnt_exist,
            "Should show an error message about the file not existing.")
   end
 
-  should "give an error if the file is not a valid box" do
-    invalid = @environment.workdir.join("nope.txt")
+  it "gives an error if the file is not a valid box" do
+    invalid = environment.workdir.join("nope.txt")
     invalid.open("w+") do |f|
       f.write("INVALID!")
     end
@@ -45,12 +47,11 @@ class BoxTest < AcceptanceTest
            "should say the box is invalid")
   end
 
-  should "add a box from an HTTP server" do
-    # TODO: Spin up an HTTP server to serve a file, add and test.
-    skip("Need to setup HTTP server functionality")
+  it "can add a box from an HTTP server" do
+    pending("Need to setup HTTP server functionality")
   end
 
-  should "remove a box" do
+  it "can remove a box" do
     require_box("default")
 
     # Add the box, remove the box, then verify that the box no longer
@@ -63,11 +64,11 @@ class BoxTest < AcceptanceTest
            "No boxes should be installed")
   end
 
-  should "repackage a box" do
+  it "can repackage a box" do
     require_box("default")
 
     original_size = File.size(config.boxes["default"])
-    @logger.debug("Original package size: #{original_size}")
+    logger.debug("Original package size: #{original_size}")
 
     # Add the box, repackage it, and verify that a package.box is
     # dumped of relatively similar size.
@@ -75,12 +76,12 @@ class BoxTest < AcceptanceTest
     execute("vagrant", "box", "repackage", "foo")
 
     # By default, repackage should dump into package.box into the CWD
-    repackaged_file = @environment.workdir.join("package.box")
+    repackaged_file = environment.workdir.join("package.box")
     assert(repackaged_file.file?, "package.box should exist in cwd of environment")
 
     # Compare the sizes
     repackaged_size = repackaged_file.size
-    @logger.debug("Repackaged size: #{repackaged_size}")
+    logger.debug("Repackaged size: #{repackaged_size}")
     size_diff = (repackaged_size - original_size).abs
     assert(size_diff < 1000, "Sizes should be very similar")
   end
diff --git a/test/acceptance/init_test.rb b/test/acceptance/init_test.rb
index 9d4958e44..1f0f96d6a 100644
--- a/test/acceptance/init_test.rb
+++ b/test/acceptance/init_test.rb
@@ -1,8 +1,10 @@
 require File.expand_path("../base", __FILE__)
 
-class InitTest < AcceptanceTest
-  should "create a Vagrantfile in the working directory" do
-    vagrantfile = @environment.workdir.join("Vagrantfile")
+describe "vagrant init" do
+  include_context "acceptance"
+
+  it "creates a Vagrantfile in the working directory" do
+    vagrantfile = environment.workdir.join("Vagrantfile")
     assert(!vagrantfile.exist?, "Vagrantfile shouldn't exist")
 
     result = execute("vagrant", "init")
@@ -10,8 +12,8 @@ class InitTest < AcceptanceTest
     assert(vagrantfile.exist?, "Vagrantfile should exist")
   end
 
-  should "create a Vagrantfile with the box set to the given argument" do
-    vagrantfile = @environment.workdir.join("Vagrantfile")
+  it "creates a Vagrantfile with the box set to the given argument" do
+    vagrantfile = environment.workdir.join("Vagrantfile")
 
     result = execute("vagrant", "init", "foo")
     assert(result.success?, "init should succeed")
@@ -19,8 +21,8 @@ class InitTest < AcceptanceTest
            "config.vm.box should be set to 'foo'")
   end
 
-  should "create a Vagrantfile with the box URL set to the given argument" do
-    vagrantfile = @environment.workdir.join("Vagrantfile")
+  it "creates a Vagrantfile with the box URL set to the given argument" do
+    vagrantfile = environment.workdir.join("Vagrantfile")
 
     result = execute("vagrant", "init", "foo", "bar")
     assert(result.success?, "init should succeed")
diff --git a/test/acceptance/ssh_test.rb b/test/acceptance/ssh_test.rb
index f56e0fdca..32842c960 100644
--- a/test/acceptance/ssh_test.rb
+++ b/test/acceptance/ssh_test.rb
@@ -1,14 +1,16 @@
 require File.expand_path("../base", __FILE__)
 
-class SSHTest < AcceptanceTest
-  should "fail if no Vagrantfile is found" do
+describe "vagrant ssh" do
+  include_context "acceptance"
+
+  it "fails if no Vagrantfile is found" do
     result = execute("vagrant", "ssh")
     assert(!result.success?, "vagrant ssh should fail")
     assert(output(result.stdout).no_vagrantfile,
            "Vagrant should error since there is no Vagrantfile")
   end
 
-  should "fail if the virtual machine is not created" do
+  it "fails if the virtual machine is not created" do
     assert_execute("vagrant", "init")
 
     result = execute("vagrant", "ssh")
@@ -17,7 +19,7 @@ class SSHTest < AcceptanceTest
            "Vagrant should error that the VM must be created.")
   end
 
-  should "be able to SSH into a running virtual machine" do
+  it "is able to SSH into a running virtual machine" do
     assert_execute("vagrant", "box", "add", "base", config.boxes["default"])
     assert_execute("vagrant", "init")
     assert_execute("vagrant", "up")
@@ -35,7 +37,7 @@ class SSHTest < AcceptanceTest
                  "Vagrant should bring up a virtual machine and be able to SSH in.")
   end
 
-  should "be able to execute a single command via the command line" do
+  it "is able to execute a single command via the command line" do
     assert_execute("vagrant", "box", "add", "base", config.boxes["default"])
     assert_execute("vagrant", "init")
     assert_execute("vagrant", "up")
diff --git a/test/acceptance/support/base_context.rb b/test/acceptance/support/base_context.rb
new file mode 100644
index 000000000..5983a6229
--- /dev/null
+++ b/test/acceptance/support/base_context.rb
@@ -0,0 +1,58 @@
+require File.expand_path("../isolated_environment", __FILE__)
+require File.expand_path("../output", __FILE__)
+require File.expand_path("../virtualbox", __FILE__)
+
+shared_context "acceptance" do
+  # Setup variables for the loggers of this test. These can be used to
+  # create more verbose logs for tests which can be useful in the case
+  # that a test fails.
+  let(:logger_name) { "logger" }
+  let(:logger) { Log4r::Logger.new("acceptance::#{logger_name}") }
+
+  # This is the global configuration given by the acceptance test
+  # configurations.
+  let(:config) { $acceptance_options }
+
+  # Setup the environment so that we have an isolated area
+  # to run Vagrant. We do some configuration here as well in order
+  # to replace "vagrant" with the proper path to Vagrant as well
+  # as tell the isolated environment about custom environmental
+  # variables to pass in.
+  let!(:environment) do
+    apps = { "vagrant" => config.vagrant_path }
+    Acceptance::IsolatedEnvironment.new(apps, config.env)
+  end
+
+  before(:each) do
+    # Wait for VBoxSVC to disappear, since each test requires its
+    # own isolated VirtualBox process.
+    Acceptance::VirtualBox.wait_for_vboxsvc
+  end
+
+  after(:each) do
+    environment.close
+  end
+
+  # Executes the given command in the context of the isolated environment.
+  #
+  # @return [Object]
+  def execute(*args, &block)
+    environment.execute(*args, &block)
+  end
+
+  # Returns an output matcher for the given text.
+  #
+  # @return [Acceptance::Output]
+  def output(text)
+    Acceptance::Output.new(text)
+  end
+
+  # This method is an assertion helper for asserting that a process
+  # succeeds. It is a wrapper around `execute` that asserts that the
+  # exit status was successful.
+  def assert_execute(*args, &block)
+    result = execute(*args, &block)
+    assert(result.success?, "expected '#{args.join(" ")}' to succeed")
+    result
+  end
+end
diff --git a/test/acceptance/helpers/config.rb b/test/acceptance/support/config.rb
similarity index 100%
rename from test/acceptance/helpers/config.rb
rename to test/acceptance/support/config.rb
diff --git a/test/acceptance/helpers/isolated_environment.rb b/test/acceptance/support/isolated_environment.rb
similarity index 100%
rename from test/acceptance/helpers/isolated_environment.rb
rename to test/acceptance/support/isolated_environment.rb
diff --git a/test/acceptance/helpers/output.rb b/test/acceptance/support/output.rb
similarity index 100%
rename from test/acceptance/helpers/output.rb
rename to test/acceptance/support/output.rb
diff --git a/test/acceptance/helpers/tempdir.rb b/test/acceptance/support/tempdir.rb
similarity index 100%
rename from test/acceptance/helpers/tempdir.rb
rename to test/acceptance/support/tempdir.rb
diff --git a/test/acceptance/helpers/virtualbox.rb b/test/acceptance/support/virtualbox.rb
similarity index 100%
rename from test/acceptance/helpers/virtualbox.rb
rename to test/acceptance/support/virtualbox.rb
diff --git a/test/acceptance/up_basic_test.rb b/test/acceptance/up_basic_test.rb
index abb3a58ec..2320573cf 100644
--- a/test/acceptance/up_basic_test.rb
+++ b/test/acceptance/up_basic_test.rb
@@ -1,14 +1,14 @@
 require File.expand_path("../base", __FILE__)
 
-class UpBasicTest < AcceptanceTest
-  should "fail if not Vagrantfile is found" do
+describe "vagrant up", "basics" do
+  it "fails if not Vagrantfile is found" do
     result = execute("vagrant", "up")
     assert(!result.success?, "vagrant up should fail")
     assert(output(result.stdout).no_vagrantfile,
            "Vagrant should error since there is no Vagrantfile")
   end
 
-  should "bring up a running virtual machine" do
+  it "brings up a running virtual machine" do
     assert_execute("vagrant", "box", "add", "base", config.boxes["default"])
     assert_execute("vagrant", "init")
     assert_execute("vagrant", "up")
diff --git a/test/acceptance/vagrant_test.rb b/test/acceptance/vagrant_test.rb
index b3f985002..c872d60f1 100644
--- a/test/acceptance/vagrant_test.rb
+++ b/test/acceptance/vagrant_test.rb
@@ -1,10 +1,12 @@
 require File.expand_path("../base", __FILE__)
 
-# NOTE: Many tests in this test suite require the `expect`
-# tool to be installed, because `expect` will launch with a
-# PTY.
-class VagrantTestColorOutput < AcceptanceTest
-  def has_expect?
+describe "vagrant and color output" do
+  include_context "acceptance"
+
+  # This is a check to see if the `expect` program is installed on this
+  # computer. Some tests require this and if this doesn't exist then the
+  # test itself will be skipped.
+  def self.has_expect?
     `which expect`
     $?.success?
   end
@@ -16,12 +18,10 @@ class VagrantTestColorOutput < AcceptanceTest
     text.index("\e[31m")
   end
 
-  should "output color if there is a TTY" do
-    skip("Test requires `expect`") if !has_expect?
-
-    @environment.workdir.join("color.exp").open("w+") do |f|
+  it "outputs color if there is a TTY", :if => has_expect? do
+    environment.workdir.join("color.exp").open("w+") do |f|
       f.puts(<<-SCRIPT)
-spawn #{@environment.replace_command("vagrant")} status
+spawn #{environment.replace_command("vagrant")} status
 expect default {}
 SCRIPT
     end
@@ -30,12 +30,10 @@ SCRIPT
     assert(has_color?(result.stdout), "output should contain color")
   end
 
-  should "not output color if there is a TTY but --no-color is present" do
-    skip("Test requires `expect`") if !has_expect?
-
-    @environment.workdir.join("color.exp").open("w+") do |f|
+  it "doesn't output color if there is a TTY but --no-color is present", :if => has_expect? do
+    environment.workdir.join("color.exp").open("w+") do |f|
       f.puts(<<-SCRIPT)
-spawn #{@environment.replace_command("vagrant")} status --no-color
+spawn #{environment.replace_command("vagrant")} status --no-color
 expect default {}
 SCRIPT
     end
@@ -44,7 +42,7 @@ SCRIPT
     assert(!has_color?(result.stdout), "output should not contain color")
   end
 
-  should "not output color in the absense of a TTY" do
+  it "doesn't output color in the absense of a TTY" do
     # This should always output an error, which on a TTY would
     # output color. We check that this doesn't output color.
     # If `vagrant status` itself is broken, another acceptance test
diff --git a/test/acceptance/version_test.rb b/test/acceptance/version_test.rb
index 5c03bf319..b8215bcbf 100644
--- a/test/acceptance/version_test.rb
+++ b/test/acceptance/version_test.rb
@@ -1,19 +1,21 @@
 require File.expand_path("../base", __FILE__)
 
-class VersionTest < AcceptanceTest
-  should "print the version to stdout" do
+describe "vagrant version" do
+  include_context "acceptance"
+
+  it "prints the version to stdout" do
     result = execute("vagrant", "version")
     assert(output(result.stdout).is_version?(config.vagrant_version),
            "output should be version")
   end
 
-  should "print the version with '-v'" do
+  it "prints the version when called with '-v'" do
     result = execute("vagrant", "-v")
     assert(output(result.stdout).is_version?(config.vagrant_version),
            "output should be version")
   end
 
-  should "print the version with '--version'" do
+  it "prints the version when called with '--version'" do
     result = execute("vagrant", "--version")
     assert(output(result.stdout).is_version?(config.vagrant_version),
            "output should be version")
diff --git a/vagrant.gemspec b/vagrant.gemspec
index 34762a619..a981326f8 100644
--- a/vagrant.gemspec
+++ b/vagrant.gemspec
@@ -30,6 +30,8 @@ Gem::Specification.new do |s|
   s.add_development_dependency "mocha"
   s.add_development_dependency "posix-spawn", "~> 0.3.6"
   s.add_development_dependency "sys-proctable", "~> 0.9.1"
+  s.add_development_dependency "rspec-core", "~> 2.7.1"
+  s.add_development_dependency "rspec-mocks", "~> 2.7.0"
 
   s.files         = `git ls-files`.split("\n")
   s.executables   = `git ls-files`.split("\n").map{|f| f =~ /^bin\/(.*)/ ? $1 : nil}.compact