diff --git a/bin/vagrant b/bin/vagrant
index f0d638074..d515430ee 100755
--- a/bin/vagrant
+++ b/bin/vagrant
@@ -29,7 +29,7 @@ argv.each_index do |i|
       ENV['VAGRANT_NO_PLUGINS'] = "1"
     end
 
-    if arg == "plugin" && ["repair", "expunge"].include?(argv[i+1])
+    if arg == "plugin" && argv[i+1] != "list"
       ENV['VAGRANT_DISABLE_PLUGIN_INIT'] = "1"
     end
 
diff --git a/lib/vagrant.rb b/lib/vagrant.rb
index 683137e8d..e2603026e 100644
--- a/lib/vagrant.rb
+++ b/lib/vagrant.rb
@@ -248,7 +248,15 @@ plugins = Vagrant::Plugin::Manager.instance.installed_plugins
 
 global_logger.info("Plugins:")
 plugins.each do |plugin_name, plugin_info|
-  global_logger.info("  - #{plugin_name} = #{plugin_info["installed_gem_version"]}")
+  installed_version = plugin_info["installed_gem_version"]
+  version_constraint = plugin_info["gem_version"]
+  installed_version = 'undefined' if installed_version.to_s.empty?
+  version_constraint = '> 0' if version_constraint.to_s.empty?
+  global_logger.info(
+    "  - #{plugin_name} = [installed: " \
+      "#{installed_version} constraint: " \
+      "#{version_constraint}]"
+  )
 end
 
 if Vagrant.plugins_init?
diff --git a/lib/vagrant/bundler.rb b/lib/vagrant/bundler.rb
index 284152890..74941b100 100644
--- a/lib/vagrant/bundler.rb
+++ b/lib/vagrant/bundler.rb
@@ -48,28 +48,11 @@ module Vagrant
       # Never allow dependencies to be remotely satisfied during init
       request_set.remote = false
 
-      # Sets that we can resolve our dependencies from
-      current_set = Gem::Resolver::CurrentSet.new
-      plugin_set = Gem::Resolver::VendorSet.new
       repair_result = nil
       begin
-        # Register all known plugin specifications to the plugin set
-        Dir.glob(plugin_gem_path.join('specifications/*.gemspec').to_s).each do |spec_path|
-          spec = Gem::Specification.load(spec_path)
-          desired_spec_path = File.join(spec.gem_dir, "#{spec.name}.gemspec")
-          # Vendor set requires the spec to be within the gem directory. Some gems will package their
-          # spec file, and that's not what we want to load.
-          if !File.exist?(desired_spec_path) || !FileUtils.cmp(spec.spec_file, desired_spec_path)
-            File.write(desired_spec_path, spec.to_ruby)
-          end
-          plugin_set.add_vendor_gem(spec.name, spec.gem_dir)
-        end
-
         # Compose set for resolution
-        composed_set = Gem::Resolver.compose_sets(current_set, plugin_set)
-
+        composed_set = generate_vagrant_set
         @logger.debug("Composed local RubyGems set for plugin init resolution: #{composed_set}")
-
         # Resolve the request set to ensure proper activation order
         solution = request_set.resolve(composed_set)
       rescue Gem::UnsatisfiableDependencyError => failure
@@ -93,34 +76,7 @@ module Vagrant
       end
 
       # Activate the gems
-      retried = false
-      begin
-        @logger.debug("Initialization solution set: #{solution.map(&:full_name)}")
-        solution.each do |activation_request|
-          unless activation_request.full_spec.activated?
-            @logger.debug("Activating gem #{activation_request.full_spec.full_name}")
-            activation_request.full_spec.activate
-            if(defined?(::Bundler))
-              @logger.debug("Marking gem #{activation_request.full_spec.full_name} loaded within Bundler.")
-              ::Bundler.rubygems.mark_loaded activation_request.full_spec
-            end
-          end
-        end
-      rescue Gem::LoadError => e
-        # Depending on the version of Ruby, the ordering of the solution set
-        # will be either 0..n (molinillo) or n..0 (pre-molinillo). Instead of
-        # attempting to determine what's in use, or if it has some how changed
-        # again, just reverse order on failure and attempt again.
-        if retried
-          @logger.error("Failed to load solution set - #{e.class}: #{e}")
-          raise
-        else
-          @logger.debug("Failed to load solution set. Retrying with reverse order.")
-          retried = true
-          solution.reverse!
-          retry
-        end
-      end
+      activate_solution(solution)
 
       full_vagrant_spec_list = Gem::Specification.find_all{true} +
         solution.map(&:full_spec)
@@ -172,7 +128,7 @@ module Vagrant
     #   empty or nil, all plugins will be updated.
     def update(plugins, specific)
       specific ||= []
-      update = { gems: specific } if !specific.empty?
+      update = {gems: specific.empty? ? true : specific}
       internal_install(plugins, update)
     end
 
@@ -180,7 +136,10 @@ module Vagrant
     def clean(plugins)
       # Generate dependencies for all registered plugins
       plugin_deps = plugins.map do |name, info|
-        Gem::Dependency.new(name, info['gem_version'].to_s.empty? ? '> 0' : info['gem_version'])
+        gem_version = info['installed_gem_version']
+        gem_version = info['gem_version'] if gem_version.to_s.empty?
+        gem_version = "> 0" if gem_version.to_s.empty?
+        Gem::Dependency.new(name, gem_version)
       end
 
       # Load dependencies into a request set for resolution
@@ -191,7 +150,7 @@ module Vagrant
       # Sets that we can resolve our dependencies from. Note that we only
       # resolve from the current set as all required deps are activated during
       # init.
-      current_set = Gem::Resolver::CurrentSet.new
+      current_set = generate_vagrant_set
 
       # Collect all plugin specifications
       plugin_specs = Dir.glob(plugin_gem_path.join('specifications/*.gemspec').to_s).map do |spec_path|
@@ -201,15 +160,19 @@ module Vagrant
       # Resolve the request set to ensure proper activation order
       solution = request_set.resolve(current_set)
       solution_specs = solution.map(&:full_spec)
+      solution_full_names = solution_specs.map(&:full_name)
 
       # Find all specs installed to plugins directory that are not
       # found within the solution set
       plugin_specs.delete_if do |spec|
-        solution.include?(spec)
+        solution_full_names.include?(spec.full_name)
       end
 
+      @logger.debug("Specifications to be removed - #{plugin_specs.map(&:full_name)}")
+
       # Now delete all unused specs
       plugin_specs.each do |spec|
+        @logger.debug("Uninstalling gem - #{spec.full_name}")
         Gem::Uninstaller.new(spec.name,
           version: spec.version,
           install_dir: plugin_gem_path,
@@ -241,13 +204,15 @@ module Vagrant
       # Only allow defined Gem sources
       Gem.sources.clear
 
-      update = {} unless update.is_a?(Hash)
+      update = {} if !update.is_a?(Hash)
+      skips = []
       installer_set = Gem::Resolver::InstallerSet.new(:both)
 
       # Generate all required plugin deps
       plugin_deps = plugins.map do |name, info|
-        if update == true || (update[:gems].respond_to?(:include?) && update[:gems].include?(name))
+        if update[:gems] == true || (update[:gems].respond_to?(:include?) && update[:gems].include?(name))
           gem_version = '> 0'
+          skips << name
         else
           gem_version = info['gem_version'].to_s.empty? ? '> 0' : info['gem_version']
         end
@@ -277,26 +242,136 @@ module Vagrant
       # gems that are incompatible with the core system
       request_set.import(existing_deps)
 
+      installer_set = Gem::Resolver.compose_sets(installer_set, generate_plugin_set(skips))
+
       # Generate the required solution set for new plugins
       solution = request_set.resolve(installer_set)
-
-      @logger.debug("Generated solution set: #{solution.map(&:full_name)}")
-
-      # If any items in the solution set are local but not activated, turn them on
-      solution.each do |activation_request|
-        if activation_request.installed? && !activation_request.full_spec.activated?
-          @logger.debug("Activating gem specification: #{activation_request.full_spec.full_name}")
-          activation_request.full_spec.activate
-        end
-      end
+      activate_solution(solution)
 
       # Install all remote gems into plugin path. Set the installer to ignore dependencies
       # as we know the dependencies are satisfied and it will attempt to validate a gem's
       # dependencies are satisified by gems in the install directory (which will likely not
       # be true)
       result = request_set.install_into(plugin_gem_path.to_s, true, ignore_dependencies: true)
-      result.map(&:full_spec)
+      result = result.map(&:full_spec)
+      result
     end
 
+    # Generate the composite resolver set totally all of vagrant (builtin + plugin set)
+    def generate_vagrant_set
+      Gem::Resolver.compose_sets(generate_builtin_set, generate_plugin_set)
+    end
+
+    # Generate the builtin resolver set
+    def generate_builtin_set
+      Gem::Resolver::CurrentSet.new
+    end
+
+    # Generate the plugin resolver set. Optionally provide specification names (short or
+    # full) that should be ignored
+    def generate_plugin_set(skip=[])
+      plugin_set = PluginSet.new
+      @logger.debug("Generating new plugin set instance. Skip gems - #{skip}")
+      Dir.glob(plugin_gem_path.join('specifications/*.gemspec').to_s).each do |spec_path|
+        spec = Gem::Specification.load(spec_path)
+        desired_spec_path = File.join(spec.gem_dir, "#{spec.name}.gemspec")
+        # Vendor set requires the spec to be within the gem directory. Some gems will package their
+        # spec file, and that's not what we want to load.
+        if !File.exist?(desired_spec_path) || !FileUtils.cmp(spec.spec_file, desired_spec_path)
+          File.write(desired_spec_path, spec.to_ruby)
+        end
+        next if skip.include?(spec.name) || skip.include?(spec.full_name)
+        plugin_set.add_vendor_gem(spec.name, spec.gem_dir)
+      end
+      plugin_set
+    end
+
+    # Activate a given solution
+    def activate_solution(solution)
+      retried = false
+      begin
+        @logger.debug("Activating solution set: #{solution.map(&:full_name)}")
+        solution.each do |activation_request|
+          unless activation_request.full_spec.activated?
+            @logger.debug("Activating gem #{activation_request.full_spec.full_name}")
+            activation_request.full_spec.activate
+            if(defined?(::Bundler))
+              @logger.debug("Marking gem #{activation_request.full_spec.full_name} loaded within Bundler.")
+              ::Bundler.rubygems.mark_loaded activation_request.full_spec
+            end
+          end
+        end
+      rescue Gem::LoadError => e
+        # Depending on the version of Ruby, the ordering of the solution set
+        # will be either 0..n (molinillo) or n..0 (pre-molinillo). Instead of
+        # attempting to determine what's in use, or if it has some how changed
+        # again, just reverse order on failure and attempt again.
+        if retried
+          @logger.error("Failed to load solution set - #{e.class}: #{e}")
+          raise
+        else
+          @logger.debug("Failed to load solution set. Retrying with reverse order.")
+          retried = true
+          solution.reverse!
+          retry
+        end
+      end
+    end
+
+    # This is a custom Gem::Resolver::Set for use with Vagrant plugins. It is
+    # a modified Gem::Resolver::VendorSet that supports multiple versions of
+    # a specific gem
+    class PluginSet < Gem::Resolver::VendorSet
+      ##
+      # Adds a specification to the set with the given +name+ which has been
+      # unpacked into the given +directory+.
+      def add_vendor_gem(name, directory)
+        gemspec = File.join(directory, "#{name}.gemspec")
+        spec = Gem::Specification.load(gemspec)
+        if !spec
+          raise Gem::GemNotFoundException,
+            "unable to find #{gemspec} for gem #{name}"
+        end
+
+        spec.full_gem_path = File.expand_path(directory)
+
+        @specs[spec.name] ||= []
+        @specs[spec.name] << spec
+        @directories[spec] = directory
+
+        spec
+      end
+
+      ##
+      # Returns an Array of VendorSpecification objects matching the
+      # DependencyRequest +req+.
+      def find_all(req)
+        @specs.values.flatten.select do |spec|
+          req.match?(spec)
+        end.map do |spec|
+          source = Gem::Source::Vendor.new(@directories[spec])
+          Gem::Resolver::VendorSpecification.new(self, spec, source)
+        end
+      end
+
+      ##
+      # Loads a spec with the given +name+. +version+, +platform+ and +source+ are
+      # ignored.
+      def load_spec (name, version, platform, source)
+        version = Gem::Version.new(version) if !version.is_a?(Gem::Version)
+        @specs.fetch(name, []).detect{|s| s.name == name && s.version = version}
+      end
+    end
+  end
+end
+
+# Patch for Ruby 2.2 and Bundler to behave properly when uninstalling plugins
+if Gem::Version.new(RUBY_VERSION) < Gem::Version.new('2.3')
+  if defined?(::Bundler) && !::Bundler::SpecSet.instance_methods.include?(:delete)
+    class Gem::Specification
+      def self.remove_spec(spec)
+        Gem::Specification.reset
+      end
+    end
   end
 end
diff --git a/lib/vagrant/errors.rb b/lib/vagrant/errors.rb
index 2139f994b..494f0071b 100644
--- a/lib/vagrant/errors.rb
+++ b/lib/vagrant/errors.rb
@@ -588,6 +588,10 @@ module Vagrant
       error_key(:plugin_uninstall_system)
     end
 
+    class PluginInitError < VagrantError
+      error_key(:plugin_init_error)
+    end
+
     class PushesNotDefined < VagrantError
       error_key(:pushes_not_defined)
     end
diff --git a/lib/vagrant/plugin/manager.rb b/lib/vagrant/plugin/manager.rb
index 72b291a3e..4f875fd6f 100644
--- a/lib/vagrant/plugin/manager.rb
+++ b/lib/vagrant/plugin/manager.rb
@@ -80,9 +80,13 @@ module Vagrant
           version: opts[:version],
           require: opts[:require],
           sources: opts[:sources],
-          installed_gem_version: result.version
+          installed_gem_version: result.version.to_s
         )
 
+        # After install clean plugin gems to remove any cruft. This is useful
+        # for removing outdated dependencies or other versions of an installed
+        # plugin if the plugin is upgraded/downgraded
+        Vagrant::Bundler.instance.clean(installed_plugins)
         result
       rescue Gem::GemNotFoundException
         raise Errors::PluginGemNotFound, name: name
@@ -111,7 +115,23 @@ module Vagrant
 
       # Updates all or a specific set of plugins.
       def update_plugins(specific)
-        Vagrant::Bundler.instance.update(installed_plugins, specific)
+        result = Vagrant::Bundler.instance.update(installed_plugins, specific)
+        installed_plugins.each do |name, info|
+          matching_spec = result.detect{|s| s.name == name}
+          info = Hash[
+            info.map do |key, value|
+              [key.to_sym, value]
+            end
+          ]
+          if matching_spec
+            @user_file.add_plugin(name, **info.merge(
+              version: "> 0",
+              installed_gem_version: matching_spec.version.to_s
+            ))
+          end
+        end
+        Vagrant::Bundler.instance.clean(installed_plugins)
+        result
       rescue Gem::Exception => e
         raise Errors::BundlerError, message: e.to_s
       end
diff --git a/lib/vagrant/plugin/state_file.rb b/lib/vagrant/plugin/state_file.rb
index c80ee658c..85db50b92 100644
--- a/lib/vagrant/plugin/state_file.rb
+++ b/lib/vagrant/plugin/state_file.rb
@@ -31,11 +31,12 @@ module Vagrant
       # @param [String] name The name of the plugin
       def add_plugin(name, **opts)
         @data["installed"][name] = {
-          "ruby_version"    => RUBY_VERSION,
-          "vagrant_version" => Vagrant::VERSION,
-          "gem_version"     => opts[:version] || "",
-          "require"         => opts[:require] || "",
-          "sources"         => opts[:sources] || [],
+          "ruby_version"          => RUBY_VERSION,
+          "vagrant_version"       => Vagrant::VERSION,
+          "gem_version"           => opts[:version] || "",
+          "require"               => opts[:require] || "",
+          "sources"               => opts[:sources] || [],
+          "installed_gem_version" => opts[:installed_gem_version]
         }
 
         save!
diff --git a/plugins/commands/plugin/action/update_gems.rb b/plugins/commands/plugin/action/update_gems.rb
index 57414273f..f59fce996 100644
--- a/plugins/commands/plugin/action/update_gems.rb
+++ b/plugins/commands/plugin/action/update_gems.rb
@@ -19,17 +19,15 @@ module VagrantPlugins
           end
 
           manager = Vagrant::Plugin::Manager.instance
-          installed_specs = manager.installed_specs
+          installed_plugins = manager.installed_plugins
           new_specs       = manager.update_plugins(names)
+          updated_plugins = manager.installed_plugins
 
           updated = {}
-          installed_specs.each do |ispec|
-            new_specs.each do |uspec|
-              next if uspec.name != ispec.name
-              next if ispec.version >= uspec.version
-              next if updated[uspec.name] && updated[uspec.name].version >= uspec.version
-
-              updated[uspec.name] = uspec
+          installed_plugins.each do |name, info|
+            update = updated_plugins[name]
+            if update && update["installed_gem_version"] != info["installed_gem_version"]
+              updated[name] = update["installed_gem_version"]
             end
           end
 
@@ -37,9 +35,9 @@ module VagrantPlugins
             env[:ui].success(I18n.t("vagrant.commands.plugin.up_to_date"))
           end
 
-          updated.values.each do |spec|
+          updated.each do |name, version|
             env[:ui].success(I18n.t("vagrant.commands.plugin.updated",
-                                    name: spec.name, version: spec.version.to_s))
+                                    name: name, version: version.to_s))
           end
 
           # Continue
diff --git a/test/unit/plugins/commands/plugin/action/update_gems_test.rb b/test/unit/plugins/commands/plugin/action/update_gems_test.rb
index 50e56267b..a3b4661c2 100644
--- a/test/unit/plugins/commands/plugin/action/update_gems_test.rb
+++ b/test/unit/plugins/commands/plugin/action/update_gems_test.rb
@@ -18,12 +18,14 @@ describe VagrantPlugins::CommandPlugin::Action::UpdateGems do
   describe "#call" do
     it "should update all plugins if none are specified" do
       expect(manager).to receive(:update_plugins).with([]).once.and_return([])
+      expect(manager).to receive(:installed_plugins).twice.and_return({})
       expect(app).to receive(:call).with(env).once
       subject.call(env)
     end
 
     it "should update specified plugins" do
       expect(manager).to receive(:update_plugins).with(["foo"]).once.and_return([])
+      expect(manager).to receive(:installed_plugins).twice.and_return({})
       expect(app).to receive(:call).with(env).once
 
       env[:plugin_name] = ["foo"]
diff --git a/test/unit/vagrant/plugin/manager_test.rb b/test/unit/vagrant/plugin/manager_test.rb
index f328d9ea2..da94c6ea6 100644
--- a/test/unit/vagrant/plugin/manager_test.rb
+++ b/test/unit/vagrant/plugin/manager_test.rb
@@ -34,6 +34,7 @@ describe Vagrant::Plugin::Manager do
         expect(plugins).to have_key("foo")
         expect(local).to be_false
       }.and_return(specs)
+      expect(bundler).to receive(:clean)
 
       result = subject.install_plugin("foo")
 
@@ -70,6 +71,7 @@ describe Vagrant::Plugin::Manager do
         ordered.and_return(local_spec)
 
       expect(bundler).not_to receive(:install)
+      expect(bundler).to receive(:clean)
 
       subject.install_plugin(name)
 
@@ -95,6 +97,7 @@ describe Vagrant::Plugin::Manager do
           expect(plugins["foo"]["gem_version"]).to eql(">= 0.1.0")
           expect(local).to be_false
         }.and_return(specs)
+        expect(bundler).to receive(:clean)
 
         subject.install_plugin("foo", version: ">= 0.1.0")
 
@@ -109,6 +112,7 @@ describe Vagrant::Plugin::Manager do
           expect(plugins["foo"]["gem_version"]).to eql("0.1.0")
           expect(local).to be_false
         }.and_return(specs)
+        expect(bundler).to receive(:clean)
 
         subject.install_plugin("foo", version: "0.1.0")
 
diff --git a/test/unit/vagrant/plugin/state_file_test.rb b/test/unit/vagrant/plugin/state_file_test.rb
index a0fbccf66..ec50f3cba 100644
--- a/test/unit/vagrant/plugin/state_file_test.rb
+++ b/test/unit/vagrant/plugin/state_file_test.rb
@@ -26,11 +26,12 @@ describe Vagrant::Plugin::StateFile do
       plugins = instance.installed_plugins
       expect(plugins.length).to eql(1)
       expect(plugins["foo"]).to eql({
-        "ruby_version"    => RUBY_VERSION,
-        "vagrant_version" => Vagrant::VERSION,
-        "gem_version"     => "",
-        "require"         => "",
-        "sources"         => [],
+        "ruby_version"          => RUBY_VERSION,
+        "vagrant_version"       => Vagrant::VERSION,
+        "gem_version"           => "",
+        "require"               => "",
+        "sources"               => [],
+        "installed_gem_version" => nil,
       })
     end