diff --git a/lib/vagrant/environment.rb b/lib/vagrant/environment.rb
index 1f15b6c62..46899197c 100644
--- a/lib/vagrant/environment.rb
+++ b/lib/vagrant/environment.rb
@@ -740,21 +740,34 @@ module Vagrant
         end
       end
 
+      # This keeps track of the old plugins that need to be reinstalled
+      # because they were installed with an old version of Ruby.
+      reinstall = []
+
       # Load the plugins
       plugins_json_file = @home_path.join("plugins.json")
       @logger.debug("Loading plugins from: #{plugins_json_file}")
-      if plugins_json_file.file?
-        data = JSON.parse(plugins_json_file.read)
-        data["installed"].each do |plugin|
-          @logger.info("Loading plugin from JSON: #{plugin}")
-          begin
-            Vagrant.require_plugin(plugin)
-          rescue Errors::PluginLoadError => e
-            @ui.error(e.message + "\n")
-          rescue Errors::PluginLoadFailed => e
-            @ui.error(e.message + "\n")
-          end
+      state = VagrantPlugins::CommandPlugin::StateFile.new(plugins_json_file)
+      state.installed_plugins.each do |name, extra|
+        # If the Ruby version changed, then they need to reinstall the plugin
+        if extra["ruby_version"] != RUBY_VERSION
+          reinstall << name
+          next
         end
+
+        @logger.info("Loading plugin from JSON: #{plugin}")
+        begin
+          Vagrant.require_plugin(plugin)
+        rescue Errors::PluginLoadError => e
+          @ui.error(e.message + "\n")
+        rescue Errors::PluginLoadFailed => e
+          @ui.error(e.message + "\n")
+        end
+      end
+
+      if !reinstall.empty?
+        @ui.warn(I18n.t("vagrant.plugin_needs_reinstall",
+          names: reinstall.join(", ")))
       end
     end
 
diff --git a/plugins/commands/plugin/state_file.rb b/plugins/commands/plugin/state_file.rb
index c1543bc8f..6860bdd09 100644
--- a/plugins/commands/plugin/state_file.rb
+++ b/plugins/commands/plugin/state_file.rb
@@ -24,6 +24,7 @@ module VagrantPlugins
       def add_plugin(name)
         if !@data["installed"].has_key?(name)
           @data["installed"][name] = {
+            "ruby_version"    => RUBY_VERSION,
             "vagrant_version" => Vagrant::VERSION,
           }
         end
@@ -65,6 +66,7 @@ module VagrantPlugins
         new_installed = {}
         (@data["installed"] || []).each do |plugin|
           new_installed[plugin] = {
+            "ruby_version"    => "0",
             "vagrant_version" => "0",
           }
         end
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index f89789c63..d3cbd88c8 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -42,7 +42,6 @@ en:
       to automatically delete Chef nodes and clients.
     chef_run_list_empty: |-
       Warning: Chef run list is empty. This may not be what you want.
-
     docker_installing: |-
       Installing Docker (%{version}) onto machine...
     docker_pulling_images:
@@ -56,7 +55,23 @@ en:
     docker_auto_start_not_available: |-
       Unable to configure automatic restart of Docker containers on
       the guest machine
+    plugin_needs_reinstall: |-
+      The following plugins were installed with a version of Vagrant
+      that had different versions of underlying components. Because
+      these component versions were changed (which rarely happens),
+      the plugins must be uninstalled and reinstalled.
 
+      To ensure that all the dependencies are properly updated as well
+      it is _highly recommended_ to do a `vagrant plugin uninstall`
+      prior to reinstalling.
+
+      This message will not go away until all the plugins below are
+      either uninstalled or uninstalled then reinstalled.
+
+      The plugins below will not be loaded until they're uninstalled
+      and reinstalled:
+
+      %{names}
     provisioner_cleanup: |-
       Running cleanup tasks for '%{name}' provisioner...
 
diff --git a/test/unit/plugins/commands/plugin/state_file_test.rb b/test/unit/plugins/commands/plugin/state_file_test.rb
index 4610428b3..a29daa6c5 100644
--- a/test/unit/plugins/commands/plugin/state_file_test.rb
+++ b/test/unit/plugins/commands/plugin/state_file_test.rb
@@ -29,7 +29,10 @@ describe VagrantPlugins::CommandPlugin::StateFile do
       instance = described_class.new(path)
       plugins = instance.installed_plugins
       expect(plugins.length).to eql(1)
-      expect(plugins["foo"]).to eql({ "vagrant_version" => Vagrant::VERSION })
+      expect(plugins["foo"]).to eql({
+        "ruby_version"    => RUBY_VERSION,
+        "vagrant_version" => Vagrant::VERSION,
+      })
     end
 
     it "should remove plugins" do
@@ -63,6 +66,7 @@ describe VagrantPlugins::CommandPlugin::StateFile do
     it "should have the right installed plugins" do
       plugins = subject.installed_plugins
       expect(plugins.keys).to eql(["foo"])
+      expect(plugins["foo"]["ruby_version"]).to eql("0")
       expect(plugins["foo"]["vagrant_version"]).to eql("0")
     end
   end