diff --git a/plugins/communicators/winrm/helper.rb b/plugins/communicators/winrm/helper.rb
index 928c29979..b435a960c 100644
--- a/plugins/communicators/winrm/helper.rb
+++ b/plugins/communicators/winrm/helper.rb
@@ -33,7 +33,7 @@ module VagrantPlugins
         return addr if addr
 
         ssh_info = machine.ssh_info
-        raise Errors::WinRMNotReady if !ssh_info || ssh_info[:host].empty?
+        raise Errors::WinRMNotReady if !ssh_info || ssh_info[:host].to_s.empty?
         return ssh_info[:host]
       end
 
diff --git a/test/unit/plugins/communicators/winrm/helper_test.rb b/test/unit/plugins/communicators/winrm/helper_test.rb
index 818a4c75e..5768c720e 100644
--- a/test/unit/plugins/communicators/winrm/helper_test.rb
+++ b/test/unit/plugins/communicators/winrm/helper_test.rb
@@ -42,6 +42,12 @@ describe VagrantPlugins::CommunicatorWinRM::Helper do
       expect { subject.winrm_address(machine) }.
         to raise_error(VagrantPlugins::CommunicatorWinRM::Errors::WinRMNotReady)
     end
+
+    it "raise a WinRMNotReady exception if it detects an unset host ip" do
+      machine.stub(ssh_info: { host: nil })
+      expect { subject.winrm_address(machine) }.
+        to raise_error(VagrantPlugins::CommunicatorWinRM::Errors::WinRMNotReady)
+    end
   end
 
   describe ".winrm_info" do