diff --git a/lib/vagrant/bundler.rb b/lib/vagrant/bundler.rb
index 92ee53a40..f4d2a0239 100644
--- a/lib/vagrant/bundler.rb
+++ b/lib/vagrant/bundler.rb
@@ -480,7 +480,7 @@ module Vagrant
         if update[:gems] == true || (update[:gems].respond_to?(:include?) && update[:gems].include?(name))
           if Gem::Requirement.new(gem_version).exact?
             gem_version = "> 0"
-            @logger.debug("Detected exact version match for `#{name}` plugin update. Reset to loose constraint #{gem_version.inspect}.")
+            @logger.debug("Detected exact version match for `#{name}` plugin update. Reset to loosen constraint #{gem_version.inspect}.")
           end
           skips << name
         end
@@ -565,10 +565,10 @@ module Vagrant
       activate_solution(solution)
 
       # Remove gems which are already installed
-      request_set.sorted_requests.delete_if do |activation_req|
-        rs_spec = activation_req.spec
-        if vagrant_internal_specs.detect{|ispec| ispec.name == rs_spec.name && ispec.version == rs_spec.version }
-          @logger.debug("Removing activation request from install. Already installed. (#{rs_spec.spec.full_name})")
+      request_set.sorted_requests.delete_if do |act_req|
+        rs = act_req.spec
+        if vagrant_internal_specs.detect{ |i| i.name == rs.name && i.version == rs.version }
+          @logger.debug("Removing activation request from install. Already installed. (#{rs.spec.full_name})")
           true
         end
       end
diff --git a/lib/vagrant/errors.rb b/lib/vagrant/errors.rb
index 4271967ef..05e821bba 100644
--- a/lib/vagrant/errors.rb
+++ b/lib/vagrant/errors.rb
@@ -628,6 +628,10 @@ module Vagrant
       error_key(:plugin_install_license_not_found)
     end
 
+    class PluginInstallFailed < VagrantError
+      error_key(:plugin_install_failed)
+    end
+
     class PluginInstallSpace < VagrantError
       error_key(:plugin_install_space)
     end
diff --git a/lib/vagrant/plugin/manager.rb b/lib/vagrant/plugin/manager.rb
index 3a0863252..9058e68b3 100644
--- a/lib/vagrant/plugin/manager.rb
+++ b/lib/vagrant/plugin/manager.rb
@@ -150,17 +150,28 @@ module Vagrant
         else
           result = local_spec
         end
-        # Add the plugin to the state file
-        plugin_file = opts[:env_local] ? @local_file : @user_file
-        plugin_file.add_plugin(
-          result.name,
-          version: opts[:version],
-          require: opts[:require],
-          sources: opts[:sources],
-          env_local: !!opts[:env_local],
-          installed_gem_version: result.version.to_s
-        )
 
+        if result
+          # Add the plugin to the state file
+          plugin_file = opts[:env_local] ? @local_file : @user_file
+          plugin_file.add_plugin(
+            result.name,
+            version: opts[:version],
+            require: opts[:require],
+            sources: opts[:sources],
+            env_local: !!opts[:env_local],
+            installed_gem_version: result.version.to_s
+          )
+        else
+          r = Gem::Dependency.new(name, opts[:version])
+          result = Gem::Specification.find { |s|
+            s.satisfies_requirement?(r) &&
+              s.activated?
+          }
+          raise Errors::PluginInstallFailed,
+            name: name if result.nil?
+          @logger.warn("Plugin install returned no result as no new plugins were installed.")
+        end
         # 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
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index 7ddadd519..abb0901d9 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -1130,6 +1130,10 @@ en:
         The license file to install could not be found. Please verify
         the path you gave is correct. The path to the license file given
         was: '%{path}'
+      plugin_install_failed: |-
+        Vagrant was unable to install the requested plugin: '%{name}'
+        Please try to install this plugin again. If Vagrant is still unable
+        to install the requested plugin, please report this error.
       plugin_install_space: |-
         The directory where plugins are installed (the Vagrant home directory)
         has a space in it. On Windows, there is a bug in Ruby when compiling
diff --git a/test/unit/vagrant/plugin/manager_test.rb b/test/unit/vagrant/plugin/manager_test.rb
index 4df185f53..dcb3dbf5e 100644
--- a/test/unit/vagrant/plugin/manager_test.rb
+++ b/test/unit/vagrant/plugin/manager_test.rb
@@ -265,6 +265,25 @@ describe Vagrant::Plugin::Manager do
       expect(plugins["bar"]["gem_version"]).to eql("1.0")
     end
 
+    context "with existing activation" do
+      let(:value) { double("value") }
+
+      before do
+        expect(bundler).to receive(:install).and_return([])
+        allow(bundler).to receive(:clean)
+      end
+
+      it "should locate existing activation if available" do
+        expect(Gem::Specification).to receive(:find).and_return(value)
+        expect(subject.install_plugin("foo")).to eq(value)
+      end
+
+      it "should raise an error if no activation is located" do
+        expect(Gem::Specification).to receive(:find).and_return(nil)
+        expect { subject.install_plugin("foo") }.to raise_error(Vagrant::Errors::PluginInstallFailed)
+      end
+    end
+
     describe "installation options" do
       let(:specs) do
         specs = Array.new(5) { Gem::Specification.new }