diff --git a/plugins/communicators/winrm/shell.rb b/plugins/communicators/winrm/shell.rb
index 3bdd869db..700408940 100644
--- a/plugins/communicators/winrm/shell.rb
+++ b/plugins/communicators/winrm/shell.rb
@@ -105,7 +105,7 @@ module VagrantPlugins
               endpoint: endpoint,
               message: exception.message
         when WinRM::WinRMHTTPTransportError
-          case exception.response_code
+          case exception.status_code
           # If the error is a 401, we can return a more specific error message
           when 401
             raise Errors::AuthenticationFailed,
@@ -137,7 +137,10 @@ module VagrantPlugins
           # This is raised if we can't work out how to route traffic.
           raise Errors::NoRoute
         else
-          raise
+          raise Errors::ExecutionError,
+            shell: shell,
+            command: command,
+            message: exception.message
         end
       end
 
diff --git a/test/unit/plugins/communicators/winrm/communicator_test.rb b/test/unit/plugins/communicators/winrm/communicator_test.rb
index c73106900..1afaffffe 100644
--- a/test/unit/plugins/communicators/winrm/communicator_test.rb
+++ b/test/unit/plugins/communicators/winrm/communicator_test.rb
@@ -28,11 +28,16 @@ describe VagrantPlugins::CommunicatorWinRM::Communicator do
       expect(subject.ready?).to be_true
     end
 
-    it "returns false if hostname command fails to execute without error" do
-      expect(shell).to receive(:powershell).with("hostname").and_raise(Vagrant::Errors::VagrantError)
+    it "returns false if hostname command fails with a transient error" do
+      expect(shell).to receive(:powershell).with("hostname").and_raise(VagrantPlugins::CommunicatorWinRM::Errors::TransientError)
       expect(subject.ready?).to be_false
     end
 
+    it "raises an error if hostname command fails with an unknown error" do
+      expect(shell).to receive(:powershell).with("hostname").and_raise(Vagrant::Errors::VagrantError)
+      expect { subject.ready? }.to raise_error(Vagrant::Errors::VagrantError)
+    end
+
     it "raises timeout error when hostname command takes longer then winrm timeout" do
       expect(shell).to receive(:powershell).with("hostname") do
         sleep 2 # winrm.timeout = 1
diff --git a/test/unit/plugins/communicators/winrm/shell_test.rb b/test/unit/plugins/communicators/winrm/shell_test.rb
index 05e8351b4..7a402e3cb 100644
--- a/test/unit/plugins/communicators/winrm/shell_test.rb
+++ b/test/unit/plugins/communicators/winrm/shell_test.rb
@@ -28,11 +28,12 @@ describe VagrantPlugins::CommunicatorWinRM::WinRMShell do
       expect(subject.powershell("dir")[:exitcode]).to eq(0)
     end
 
-    it "should raise auth error when exception message contains 401" do
-      expect(session).to receive(:powershell).with(/^dir.+/).and_raise(
-        StandardError.new("Oh no! a 401 SOAP error!"))
+    it "should raise auth error when WinRM exception has a response code of 401" do
+      # The default settings might an account lockout - 20 auth failures!
+      expect(session).to receive(:powershell).with(/^dir.+/).exactly(20).times.and_raise(
+        WinRM::WinRMHTTPTransportError.new("Oh no!!", 401))
       expect { subject.powershell("dir") }.to raise_error(
-        VagrantPlugins::CommunicatorWinRM::Errors::AuthError)
+        VagrantPlugins::CommunicatorWinRM::Errors::AuthenticationFailed)
     end
 
     it "should raise an execution error when an exception occurs" do
diff --git a/test/unit/plugins/kernel_v2/config/vm_test.rb b/test/unit/plugins/kernel_v2/config/vm_test.rb
index 073e88e22..3028e2552 100644
--- a/test/unit/plugins/kernel_v2/config/vm_test.rb
+++ b/test/unit/plugins/kernel_v2/config/vm_test.rb
@@ -167,14 +167,15 @@ describe VagrantPlugins::Kernel_V2::VMConfig do
       subject.communicator = "winrm"
       subject.finalize!
       n = subject.networks
-      expect(n.length).to eq(1)
+      expect(n.length).to eq(2)
 
       # WinRM HTTP
-      expect(n[0][0]).to eq(:forwarded_port)
-      expect(n[0][1][:guest]).to eq(5985)
-      expect(n[0][1][:host]).to eq(55985)
-      expect(n[0][1][:host_ip]).to eq("127.0.0.1")
-      expect(n[0][1][:id]).to eq("winrm")
+      network = find_network("winrm")
+      # expect(n[0][0]).to eq(:forwarded_port)
+      expect(network[:guest]).to eq(5985)
+      expect(network[:host]).to eq(55985)
+      expect(network[:host_ip]).to eq("127.0.0.1")
+      expect(network[:id]).to eq("winrm")
     end
 
     it "allows overriding SSH" do