diff --git a/plugins/communicators/winrm/config.rb b/plugins/communicators/winrm/config.rb
index 7ac28404e..0e7db6f63 100644
--- a/plugins/communicators/winrm/config.rb
+++ b/plugins/communicators/winrm/config.rb
@@ -8,7 +8,7 @@ module VagrantPlugins
       attr_accessor :guest_port
       attr_accessor :max_tries
       attr_accessor :timeout
-      attr_accessor :ssl
+      attr_accessor :transport
 
       def initialize
         @username               = UNSET_VALUE
@@ -18,19 +18,20 @@ module VagrantPlugins
         @guest_port             = UNSET_VALUE
         @max_tries              = UNSET_VALUE
         @timeout                = UNSET_VALUE
-        @ssl                    = UNSET_VALUE
+        @transport              = UNSET_VALUE
         @ssl_peer_verification  = UNSET_VALUE
       end
 
       def finalize!
         @username = "vagrant" if @username == UNSET_VALUE
         @password = "vagrant" if @password == UNSET_VALUE
+        @transport = :ssl     if @transport == UNSET_VALUE
         @host = nil           if @host == UNSET_VALUE
-        @port = (@ssl ? 5986 : 5985)       if @port == UNSET_VALUE
-        @guest_port = (@ssl ? 5986 : 5985) if @guest_port == UNSET_VALUE
+        is_ssl = @transport == :ssl
+        @port = (is_ssl ? 5986 : 5985)       if @port == UNSET_VALUE
+        @guest_port = (is_ssl ? 5986 : 5985) if @guest_port == UNSET_VALUE
         @max_tries = 20       if @max_tries == UNSET_VALUE
         @timeout = 60         if @timeout == UNSET_VALUE
-        @ssl = false          if @ssl == UNSET_VALUE
         @ssl_peer_verification = true if @ssl_peer_verification == UNSET_VALUE
       end
 
diff --git a/plugins/communicators/winrm/errors.rb b/plugins/communicators/winrm/errors.rb
index 552b8a300..90c3c6dda 100644
--- a/plugins/communicators/winrm/errors.rb
+++ b/plugins/communicators/winrm/errors.rb
@@ -29,6 +29,10 @@ module VagrantPlugins
       class WinRMFileTransferError < WinRMError
         error_key(:winrm_file_transfer_error)
       end
+
+      class WinRMInvalidTransport < WinRMError
+        error_key(:invalid_transport)
+      end
     end
   end
 end
diff --git a/plugins/communicators/winrm/shell.rb b/plugins/communicators/winrm/shell.rb
index 7b3f98ae5..cd34b01fe 100644
--- a/plugins/communicators/winrm/shell.rb
+++ b/plugins/communicators/winrm/shell.rb
@@ -115,7 +115,7 @@ module VagrantPlugins
         @logger.info("  - Username: #{@config.username}")
         @logger.info("  - Transport: #{@config.transport}")
 
-        client = ::WinRM::WinRMWebService.new(endpoint, transport.to_sym, endpoint_options)
+        client = ::WinRM::WinRMWebService.new(endpoint, @config.transport.to_sym, endpoint_options)
         client.set_timeout(@config.timeout)
         client.toggle_nori_type_casting(:off) #we don't want coersion of types
         client
@@ -126,7 +126,14 @@ module VagrantPlugins
       end
 
       def endpoint
-        "http#{@ssl ? 's' : ''}://#{@host}:#{@port}/wsman"
+        case @config.transport
+        when :ssl
+          "https://#{@host}:#{@port}/wsman"
+        when :plaintext
+          "http://#{@host}:#{@port}/wsman"
+        else
+          raise Errors::WinRMInvalidTransport, transport: @config.transport
+        end
       end
 
       def endpoint_options
diff --git a/templates/locales/comm_winrm.yml b/templates/locales/comm_winrm.yml
index 9de47a9cf..8800fbbb0 100644
--- a/templates/locales/comm_winrm.yml
+++ b/templates/locales/comm_winrm.yml
@@ -29,6 +29,8 @@ en:
         Message: %{message}
       invalid_shell: |-
         %{shell} is not a supported type of Windows shell.
+      invalid_transport: |-
+        %{transport} is not a supported WinRM transport.
       winrm_not_ready: |-
         The box is not able to report an address for WinRM to connect to yet.
         WinRM cannot access this Vagrant environment. Please wait for the
diff --git a/test/unit/plugins/communicators/winrm/shell_test.rb b/test/unit/plugins/communicators/winrm/shell_test.rb
index 5b694b62d..18d2dd021 100644
--- a/test/unit/plugins/communicators/winrm/shell_test.rb
+++ b/test/unit/plugins/communicators/winrm/shell_test.rb
@@ -7,6 +7,7 @@ describe VagrantPlugins::CommunicatorWinRM::WinRMShell do
   include_context "unit"
 
   let(:session) { double("winrm_session") }
+  let(:port) { config.transport == :ssl ? 5986 : 5985 }
   let(:config)  {
     VagrantPlugins::CommunicatorWinRM::Config.new.tap do |c|
       c.username = 'username'
@@ -16,7 +17,7 @@ describe VagrantPlugins::CommunicatorWinRM::WinRMShell do
   }
 
   subject do
-    described_class.new('localhost', 5985, config).tap do |comm|
+    described_class.new('localhost', port, config).tap do |comm|
       allow(comm).to receive(:new_session).and_return(session)
     end
   end
@@ -50,15 +51,29 @@ describe VagrantPlugins::CommunicatorWinRM::WinRMShell do
   end
 
   describe ".endpoint" do
-    it "should create winrm endpoint address" do
-      expect(subject.send(:endpoint)).to eq("http://localhost:5985/wsman")
+    context 'when transport is :ssl' do
+      it "should create winrm endpoint address using https" do
+        expect(subject.send(:endpoint)).to eq("https://localhost:5986/wsman")
+      end
+    end
+
+    context "when transport is :plaintext" do
+      let(:config)  {
+        VagrantPlugins::CommunicatorWinRM::Config.new.tap do |c|
+          c.transport = :plaintext
+          c.finalize!
+        end
+      }
+      it "should create winrm endpoint address using http" do
+        expect(subject.send(:endpoint)).to eq("http://localhost:5985/wsman")
+      end
     end
   end
 
   describe ".endpoint_options" do
     it "should create endpoint options" do
       expect(subject.send(:endpoint_options)).to eq(
-        { user: "username", pass: "password", host: "localhost", port: 5985,
+        { user: "username", pass: "password", host: "localhost", port: 5986,
           basic_auth_only: true, no_ssl_peer_verification: false })
     end
   end