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/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..7df5bf170
--- /dev/null
+++ b/lib/vagrant/util/checkpoint_client.rb
@@ -0,0 +1,174 @@
+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
+
+      # Start checkpoint check
+      #
+      # @return [self]
+      def check
+        start_check
+        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 start_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
+
+    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 d8a6986c0..90eced48f 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/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"