diff --git a/plugins/communicators/winrm/plugin.rb b/plugins/communicators/winrm/plugin.rb
index a8e8b51a4..5e69cb03a 100644
--- a/plugins/communicators/winrm/plugin.rb
+++ b/plugins/communicators/winrm/plugin.rb
@@ -33,12 +33,34 @@ module VagrantPlugins
           "templates/locales/comm_winrm.yml", Vagrant.source_root)
         I18n.reload!
 
+        # Check if vagrant-winrm plugin is installed and
+        # output warning to user if found
+        if !ENV["VAGRANT_IGNORE_WINRM_PLUGIN"] &&
+            Vagrant::Plugin::Manager.instance.installed_plugins.keys.include?("vagrant-winrm")
+            $stderr.puts <<-EOF
+WARNING: Vagrant has detected the `vagrant-winrm` plugin. Vagrant ships with
+WinRM support builtin and no longer requires the `vagrant-winrm` plugin. To
+prevent unexpected errors please uninstall the `vagrant-winrm` plugin using
+the command shown below:
+
+  vagrant plugin uninstall vagrant-winrm
+
+To disable this warning, set the environment variable `VAGRANT_IGNORE_WINRM_PLUGIN`
+EOF
+        end
         # Load the WinRM gem
         require "vagrant/util/silence_warnings"
         Vagrant::Util::SilenceWarnings.silence! do
           require "winrm"
         end
       end
+
+      # @private
+      # Reset the cached init value. This is not considered a public
+      # API and should only be used for testing.
+      def self.reset!
+        send(:remove_instance_variable, :@_init)
+      end
     end
   end
 end
diff --git a/test/unit/plugins/communicators/winrm/plugin_test.rb b/test/unit/plugins/communicators/winrm/plugin_test.rb
new file mode 100644
index 000000000..298ef4f74
--- /dev/null
+++ b/test/unit/plugins/communicators/winrm/plugin_test.rb
@@ -0,0 +1,42 @@
+require File.expand_path("../../../../base", __FILE__)
+
+require Vagrant.source_root.join("plugins/communicators/winrm/plugin")
+
+describe VagrantPlugins::CommunicatorWinRM::Plugin do
+  describe "#init!" do
+    let(:manager_instance) { double("manager_instance", installed_plugins: installed_plugins) }
+    let(:installed_plugins) { {} }
+
+    before do
+      allow(I18n).to receive(:load_path).and_return("")
+      allow(I18n).to receive(:reload!)
+      allow(described_class).to receive(:require)
+      allow(Vagrant::Plugin::Manager).to receive(:instance).and_return(manager_instance)
+    end
+
+    after do
+      described_class.init!
+      described_class.reset!
+    end
+
+    it "should not output any warning" do
+      expect($stderr).not_to receive(:puts).with(/WARNING/)
+    end
+
+    context "when vagrant-winrm plugin is installed" do
+      let(:installed_plugins) { {"vagrant-winrm" => "PLUGIN_INFO"} }
+
+      it "should output a warning" do
+        expect($stderr).to receive(:puts).with(/WARNING/)
+      end
+
+      context "with VAGRANT_IGNORE_WINRM_PLUGIN set" do
+        before { allow(ENV).to receive(:[]).with("VAGRANT_IGNORE_WINRM_PLUGIN").and_return("1") }
+
+        it "should not output any warning" do
+          expect($stderr).not_to receive(:puts).with(/WARNING/)
+        end
+      end
+    end
+  end
+end
diff --git a/website/source/docs/other/environmental-variables.html.md b/website/source/docs/other/environmental-variables.html.md
index 6db684e23..21a3345e8 100644
--- a/website/source/docs/other/environmental-variables.html.md
+++ b/website/source/docs/other/environmental-variables.html.md
@@ -265,6 +265,10 @@ it will use 30 seconds as a timeout.
 Vagrant will not display the warning about disabling the core trigger feature if
 the community plugin is installed.
 
+## `VAGRANT_IGNORE_WINRM_PLUGIN`
+
+Vagrant will not display warning when `vagrant-winrm` plugin is installed.
+
 ## `VAGRANT_USER_AGENT_PROVISIONAL_STRING`
 
 Vagrant will append the contents of this variable to the default user agent header.