diff --git a/plugins/communicators/winrm/shell.rb b/plugins/communicators/winrm/shell.rb
index 2e9c35d5a..ae14e0f23 100644
--- a/plugins/communicators/winrm/shell.rb
+++ b/plugins/communicators/winrm/shell.rb
@@ -22,6 +22,7 @@ module VagrantPlugins
       @@exceptions_to_retry_on = [
         HTTPClient::KeepAliveDisconnected,
         WinRM::WinRMHTTPTransportError,
+        WinRM::WinRMAuthorizationError,
         Errno::EACCES,
         Errno::EADDRINUSE,
         Errno::ECONNREFUSED,
@@ -124,15 +125,6 @@ module VagrantPlugins
               message: exception.message
         when WinRM::WinRMHTTPTransportError
           case exception.status_code
-          # If the error is a 401, we can return a more specific error message
-          when 401
-            raise Errors::AuthenticationFailed,
-              user: @config.username,
-              password: @config.password,
-              endpoint: endpoint,
-              message: exception.message
-          end
-
           raise Errors::ExecutionError,
             shell: shell,
             command: command,
diff --git a/test/unit/plugins/communicators/winrm/shell_test.rb b/test/unit/plugins/communicators/winrm/shell_test.rb
index 7a402e3cb..22a50072d 100644
--- a/test/unit/plugins/communicators/winrm/shell_test.rb
+++ b/test/unit/plugins/communicators/winrm/shell_test.rb
@@ -31,7 +31,7 @@ describe VagrantPlugins::CommunicatorWinRM::WinRMShell do
     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))
+        WinRM::WinRMAuthorizationError.new("Oh no!!", 401))
       expect { subject.powershell("dir") }.to raise_error(
         VagrantPlugins::CommunicatorWinRM::Errors::AuthenticationFailed)
     end