diff --git a/lib/vagrant/cli.rb b/lib/vagrant/cli.rb
index cca8c0184..920828407 100644
--- a/lib/vagrant/cli.rb
+++ b/lib/vagrant/cli.rb
@@ -4,12 +4,14 @@ require 'optparse'
 module Vagrant
   # Manages the command line interface to Vagrant.
   class CLI < Vagrant.plugin("2", :command)
+
     def initialize(argv, env)
       super
 
       @logger = Log4r::Logger.new("vagrant::cli")
       @main_args, @sub_command, @sub_args = split_main_and_subcommand(argv)
 
+      Util::CheckpointClient.instance.setup(env).check
       @logger.info("CLI: #{@main_args.inspect} #{@sub_command.inspect} #{@sub_args.inspect}")
     end
 
@@ -36,6 +38,8 @@ module Vagrant
       command_class = command_plugin[0].call
       @logger.debug("Invoking command class: #{command_class} #{@sub_args.inspect}")
 
+      Util::CheckpointClient.instance.display
+
       # Initialize and execute the command class, returning the exit status.
       result = 0
       begin
diff --git a/lib/vagrant/environment.rb b/lib/vagrant/environment.rb
index 92be3d13a..581a835c9 100644
--- a/lib/vagrant/environment.rb
+++ b/lib/vagrant/environment.rb
@@ -4,7 +4,6 @@ require 'pathname'
 require 'set'
 require 'thread'
 
-require "checkpoint"
 require 'log4r'
 
 require 'vagrant/util/file_mode'
@@ -128,34 +127,6 @@ module Vagrant
       # Prepare the directories
       setup_home_path
 
-      # Run checkpoint in a background thread on every environment
-      # initialization. The cache file will cause this to mostly be a no-op
-      # most of the time.
-      @checkpoint_thr = Thread.new do
-        Thread.current[:result] = nil
-
-        # If we disabled checkpoint via env var, don't run this
-        if ENV["VAGRANT_CHECKPOINT_DISABLE"].to_s != ""
-          @logger.info("checkpoint: disabled from env var")
-          next
-        end
-
-        # If we disabled state and knowing what alerts we've seen, then
-        # disable the signature file.
-        signature_file = @data_dir.join("checkpoint_signature")
-        if ENV["VAGRANT_CHECKPOINT_NO_STATE"].to_s != ""
-          @logger.info("checkpoint: will not store state")
-          signature_file = nil
-        end
-
-        Thread.current[:result] = Checkpoint.check(
-          product: "vagrant",
-          version: VERSION,
-          signature_file: signature_file,
-          cache_file: @data_dir.join("checkpoint_cache"),
-        )
-      end
-
       # Setup the local data directory. If a configuration path is given,
       # it is expanded relative to the root path. Otherwise, we use the
       # default (which is also expanded relative to the root path).
@@ -289,16 +260,6 @@ module Vagrant
       end
     end
 
-    # Checkpoint returns the checkpoint result data. If checkpoint is
-    # disabled, this will return nil. See the hashicorp-checkpoint gem
-    # for more documentation on the return value.
-    #
-    # @return [Hash]
-    def checkpoint
-      @checkpoint_thr.join(THREAD_MAX_JOIN_TIMEOUT)
-      return @checkpoint_thr[:result]
-    end
-
     # Makes a call to the CLI with the given arguments as if they
     # came from the real command line (sometimes they do!). An example:
     #
diff --git a/lib/vagrant/util.rb b/lib/vagrant/util.rb
index cef24e8ad..32babe50d 100644
--- a/lib/vagrant/util.rb
+++ b/lib/vagrant/util.rb
@@ -1,6 +1,7 @@
 module Vagrant
   module Util
     autoload :Busy,                      'vagrant/util/busy'
+    autoload :CheckpointClient,          'vagrant/util/checkpoint_client'
     autoload :CommandDeprecation,        'vagrant/util/command_deprecation'
     autoload :Counter,                   'vagrant/util/counter'
     autoload :CredentialScrubber,        'vagrant/util/credential_scrubber'
diff --git a/lib/vagrant/util/checkpoint_client.rb b/lib/vagrant/util/checkpoint_client.rb
new file mode 100644
index 000000000..17dcfe868
--- /dev/null
+++ b/lib/vagrant/util/checkpoint_client.rb
@@ -0,0 +1,175 @@
+require "log4r"
+require "singleton"
+
+module Vagrant
+  module Util
+    class CheckpointClient
+
+      include Singleton
+
+      # Maximum number of seconds to wait for check to complete
+      CHECKPOINT_TIMEOUT = 10
+
+      # @return [Log4r::Logger]
+      attr_reader :logger
+
+      # @return [Boolean]
+      attr_reader :enabled
+
+      # @return [Hash]
+      attr_reader :files
+
+      # @return [Vagrant::Environment]
+      attr_reader :env
+
+      def initialize
+        @logger = Log4r::Logger.new("vagrant::checkpoint_client")
+        @enabled = false
+      end
+
+      # Setup will attempt to load the checkpoint library and define
+      # required paths
+      #
+      # @param [Vagrant::Environment] env
+      # @return [self]
+      def setup(env)
+        begin
+          require "checkpoint"
+          @enabled = true
+        rescue LoadError
+          @logger.warn("checkpoint library not found. disabling.")
+        end
+        @files = {
+          signature: env.data_dir.join("checkpoint_signature"),
+          cache: env.data_dir.join("checkpoint_cache")
+        }
+        @checkpoint_thread = nil
+        @env = env
+        self
+      end
+
+      # Check has completed
+      def complete?
+        !@checkpoint_thread.nil? && !@checkpoint_thread.alive?
+      end
+
+      # Result of check
+      #
+      # @return [Hash, nil]
+      def result
+        if !enabled || @checkpoint_thread.nil?
+          nil
+        elsif !defined?(@result)
+          @checkpoint_thread.join(CHECKPOINT_TIMEOUT)
+          @result = @checkpoint_thread[:result]
+        else
+          @result
+        end
+      end
+
+      # Run check
+      #
+      # @return [self]
+      def check
+        if enabled && @checkpoint_thread.nil?
+          logger.debug("starting plugin check")
+          @checkpoint_thread = Thread.new do
+            begin
+              Thread.current[:result] = Checkpoint.check(
+                product: "vagrant",
+                version: VERSION,
+                signature_file: files[:signature],
+                cache_file: files[:cache]
+              )
+              if !Thread.current[:result].is_a?(Hash)
+                Thread.current[:result] = nil
+              end
+              logger.debug("plugin check complete")
+            rescue => e
+              logger.debug("plugin check failure - #{e}")
+            end
+          end
+        end
+        self
+      end
+
+      # Display any alerts or version update information
+      #
+      # @return [boolean] true if displayed, false if not
+      def display
+        if !defined?(@displayed)
+          if !complete?
+            @logger.debug("waiting for checkpoint to complete...")
+          end
+          # Don't display if information is cached
+          if result && !result["cached"]
+            version_check
+            alerts_check
+          else
+            @logger.debug("no information received from checkpoint")
+          end
+          @displayed = true
+        else
+          false
+        end
+      end
+
+      def alerts_check
+        if result["alerts"] && !result["alerts"].empty?
+          result["alerts"].group_by{|a| a["level"]}.each_pair do |_, alerts|
+            alerts.each do |alert|
+              date = nil
+              begin
+                date = Time.at(alert["date"])
+              rescue
+                date = Time.now
+              end
+              output = I18n.t("vagrant.alert",
+                message: alert["message"],
+                date: date,
+                url: alert["url"]
+              )
+              case alert["level"]
+              when "info"
+                alert_ui = Vagrant::UI::Prefixed.new(env.ui, "vagrant")
+                alert_ui.info(output)
+              when "warn"
+                alert_ui = Vagrant::UI::Prefixed.new(env.ui, "vagrant-warning")
+                alert_ui.warn(output)
+              when "critical"
+                alert_ui = Vagrant::UI::Prefixed.new(env.ui, "vagrant-alert")
+                alert_ui.error(output)
+              end
+            end
+            env.ui.info("")
+          end
+        else
+          @logger.debug("no alert notifications to display")
+        end
+      end
+
+      def version_check
+        latest_version = Gem::Version.new(result["current_version"])
+        installed_version = Gem::Version.new(VERSION)
+        ui = Vagrant::UI::Prefixed.new(env.ui, "vagrant")
+        if latest_version > installed_version
+          @logger.info("new version of Vagrant available - #{latest_version}")
+          ui.info(I18n.t("vagrant.version_upgrade_available", latest_version: latest_version))
+          env.ui.info("")
+        else
+          @logger.debug("vagrant is currently up to date")
+        end
+      end
+
+      # @private
+      # Reset the cached values for platform. This is not considered a public
+      # API and should only be used for testing.
+      def reset!
+        logger = @logger
+        instance_variables.each(&method(:remove_instance_variable))
+        @logger = logger
+        @enabled = false
+      end
+    end
+  end
+end
diff --git a/plugins/commands/version/command.rb b/plugins/commands/version/command.rb
index c3c47acfa..95c818b48 100644
--- a/plugins/commands/version/command.rb
+++ b/plugins/commands/version/command.rb
@@ -22,7 +22,7 @@ module VagrantPlugins
         @env.ui.machine("version-installed", Vagrant::VERSION)
 
         # Load the latest information
-        cp = @env.checkpoint
+        cp = Vagrant::Util::CheckpointClient.instance.result
         if !cp
           @env.ui.output("\n"+I18n.t(
             "vagrant.version_no_checkpoint"))
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index 99f5dad2e..0f591b94c 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -1,5 +1,10 @@
 en:
   vagrant:
+    alert: |-
+      [%{date}]:
+        %{message}
+
+        - %{url}
     boot_completed: |-
       Machine booted and ready!
     boot_waiting: |-
@@ -283,6 +288,10 @@ en:
     version_no_checkpoint: |-
       Vagrant was unable to check for the latest version of Vagrant.
       Please check manually at https://www.vagrantup.com
+    version_upgrade_available: |-
+      A new version of Vagrant is available: %{latest_version}!
+      To upgrade visit: https://www.vagrantup.com/downloads.html
+
     version_upgrade_howto: |-
       To upgrade to the latest version, visit the downloads page and
       download and install the latest version of Vagrant from the URL
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
diff --git a/vagrant.gemspec b/vagrant.gemspec
index 13a08c513..d26b32adf 100644
--- a/vagrant.gemspec
+++ b/vagrant.gemspec
@@ -20,7 +20,7 @@ Gem::Specification.new do |s|
   s.add_dependency "erubis", "~> 2.7.0"
   s.add_dependency "i18n", ">= 0.6.0", "<= 0.8.0"
   s.add_dependency "listen", "~> 3.1.5"
-  s.add_dependency "hashicorp-checkpoint", "~> 0.1.1"
+  s.add_dependency "hashicorp-checkpoint", "~> 0.1.5"
   s.add_dependency "log4r", "~> 1.1.9", "< 1.1.11"
   s.add_dependency "net-ssh", "~> 4.2.0"
   s.add_dependency "net-sftp", "~> 2.1"