diff --git a/test/unit/vagrant/cli_test.rb b/test/unit/vagrant/cli_test.rb
index fb33ac62f..5d079278f 100644
--- a/test/unit/vagrant/cli_test.rb
+++ b/test/unit/vagrant/cli_test.rb
@@ -1,6 +1,7 @@
 require_relative "../base"
 
 require "vagrant/cli"
+require "vagrant/util"
 
 describe Vagrant::CLI do
   include_context "unit"
@@ -9,9 +10,21 @@ describe Vagrant::CLI do
   let(:commands) { {} }
   let(:iso_env) { isolated_environment }
   let(:env)     { iso_env.create_vagrant_env }
+  let(:checkpoint) { double("checkpoint") }
 
   before do
     allow(Vagrant.plugin("2").manager).to receive(:commands).and_return(commands)
+    allow(Vagrant::Util::CheckpointClient).to receive(:instance).and_return(checkpoint)
+    allow(checkpoint).to receive(:setup).and_return(checkpoint)
+    allow(checkpoint).to receive(:check)
+    allow(checkpoint).to receive(:display)
+  end
+
+  describe "#initialize" do
+    it "should setup checkpoint" do
+      expect(checkpoint).to receive(:check)
+      described_class.new(["destroy"], env)
+    end
   end
 
   describe "#execute" do
@@ -35,6 +48,12 @@ describe Vagrant::CLI do
       subject = described_class.new(["destroy"], env)
       expect(subject.execute).to eql(1)
     end
+
+    it "displays any checkpoint information" do
+      commands[:destroy] = [command_lambda("destroy", 42), {}]
+      expect(checkpoint).to receive(:display)
+      described_class.new(["destroy"], env).execute
+    end
   end
 
   describe "#help" do
diff --git a/test/unit/vagrant/util/checkpoint_client_test.rb b/test/unit/vagrant/util/checkpoint_client_test.rb
new file mode 100644
index 000000000..c0e038c93
--- /dev/null
+++ b/test/unit/vagrant/util/checkpoint_client_test.rb
@@ -0,0 +1,174 @@
+require File.expand_path("../../../base", __FILE__)
+
+require "vagrant/util/checkpoint_client"
+
+describe Vagrant::Util::CheckpointClient do
+  include_context "unit"
+
+  let(:iso_env) { isolated_environment }
+  let(:env)     { iso_env.create_vagrant_env }
+  let(:result) { {} }
+  let(:prefixed_ui) { double("prefixed_ui") }
+
+  subject{ Vagrant::Util::CheckpointClient.instance }
+
+  after{ subject.reset! }
+  before do
+    allow(subject).to receive(:result).and_return(result)
+    allow(Vagrant::UI::Prefixed).to receive(:new).and_return(prefixed_ui)
+  end
+
+  it "should not be enabled by default" do
+    expect(subject.enabled).to be(false)
+  end
+
+  describe "#setup" do
+    before{ subject.setup(env) }
+
+    it "should enable after setup" do
+      expect(subject.enabled).to be(true)
+    end
+
+    it "should generate required paths" do
+      expect(subject.files).not_to be_empty
+    end
+  end
+
+  describe "#check" do
+    context "without #setup" do
+      it "should not start the check" do
+        expect(Thread).not_to receive(:new)
+        subject.check
+      end
+    end
+
+    context "with setup" do
+      before{ subject.setup(env) }
+
+      it "should start the check" do
+        expect(Thread).to receive(:new)
+        subject.check
+      end
+
+      it "should call checkpoint" do
+        expect(Thread).to receive(:new).and_yield
+        expect(Checkpoint).to receive(:check)
+        subject.check
+      end
+    end
+  end
+
+  describe "#display" do
+    it "should only dislay once" do
+      expect(subject).to receive(:version_check).once
+      expect(subject).to receive(:alerts_check).once
+
+      2.times{ subject.display }
+    end
+
+    it "should not display cached information" do
+      expect(subject).to receive(:result).and_return("cached" => true).at_least(:once)
+      expect(subject).not_to receive(:version_check)
+      expect(subject).not_to receive(:alerts_check)
+
+      subject.display
+    end
+  end
+
+  describe "#alerts_check" do
+    let(:critical){
+      [{"level" => "critical", "message" => "critical message",
+        "url" => "http://example.com", "date" => Time.now.to_i}]
+    }
+    let(:warn){
+      [{"level" => "warn", "message" => "warn message",
+        "url" => "http://example.com", "date" => Time.now.to_i}]
+    }
+    let(:info){
+      [{"level" => "info", "message" => "info message",
+        "url" => "http://example.com", "date" => Time.now.to_i}]
+    }
+
+    before{ subject.setup(env) }
+
+    context "with no alerts" do
+      it "should not display alerts" do
+        expect(prefixed_ui).not_to receive(:info)
+        subject.alerts_check
+      end
+    end
+
+    context "with critical alerts" do
+      let(:result) { {"alerts" => critical} }
+
+      it "should display critical alert" do
+        expect(prefixed_ui).to receive(:error)
+        subject.alerts_check
+      end
+    end
+
+    context "with warn alerts" do
+      let(:result) { {"alerts" => warn} }
+
+      it "should display warn alerts" do
+        expect(prefixed_ui).to receive(:warn)
+        subject.alerts_check
+      end
+    end
+
+    context "with info alerts" do
+      let(:result) { {"alerts" => info} }
+
+      it "should display info alerts" do
+        expect(prefixed_ui).to receive(:info)
+        subject.alerts_check
+      end
+    end
+
+    context "with mixed alerts" do
+      let(:result) { {"alerts" => info + warn + critical} }
+
+      it "should display all alert types" do
+        expect(prefixed_ui).to receive(:info)
+        expect(prefixed_ui).to receive(:warn)
+        expect(prefixed_ui).to receive(:error)
+
+        subject.alerts_check
+      end
+    end
+  end
+
+  describe "#version_check" do
+    before{ subject.setup(env) }
+
+    let(:new_version){ Gem::Version.new(Vagrant::VERSION).bump.to_s }
+    let(:old_version){ Gem::Version.new("1.0.0") }
+
+    context "latest version is same as current version" do
+      let(:result) { {"current_version" => Vagrant::VERSION } }
+
+      it "should not display upgrade information" do
+        expect(prefixed_ui).not_to receive(:info)
+        subject.version_check
+      end
+    end
+
+    context "latest version is older than current version" do
+      let(:result) { {"current_version" => old_version} }
+
+      it "should not display upgrade information" do
+        expect(prefixed_ui).not_to receive(:info)
+        subject.version_check
+      end
+    end
+
+    context "latest version is newer than current version" do
+      let(:result) { {"current_version" => new_version} }
+
+      it "should not display upgrade information" do
+        expect(prefixed_ui).not_to receive(:info).at_least(:once)
+        subject.version_check
+      end
+    end
+  end
+end