diff --git a/plugins/communicators/winrm/communicator.rb b/plugins/communicators/winrm/communicator.rb
index 268a3c5d4..5ce188229 100644
--- a/plugins/communicators/winrm/communicator.rb
+++ b/plugins/communicators/winrm/communicator.rb
@@ -60,8 +60,8 @@ module VagrantPlugins
           command:     command,
           elevated:    false,
           error_check: true,
-          error_class: Errors::ExecutionError,
-          error_key:   :execution_error,
+          error_class: Errors::WinRMBadExitStatus,
+          error_key:   nil, # use the error_class message key
           good_exit:   0,
           shell:       :powershell,
         }.merge(opts || {})
@@ -154,10 +154,17 @@ module VagrantPlugins
       end
 
       def raise_execution_error(output, opts)
-        # The error classes expect the translation key to be _key, but that makes for an ugly
-        # configuration parameter, so we set it here from `error_key`
-        msg = "Command execution failed with an exit code of #{output[:exitcode]}"
-        error_opts = opts.merge(_key: opts[:error_key], message: msg)
+        # WinRM can return multiple stderr and stdout entries
+        error_opts = opts.merge(
+          stdout: output[:data].collect { |e| e[:stdout] }.join,
+          stderr: output[:data].collect { |e| e[:stderr] }.join
+        )
+
+        # Use a different error message key if the caller gave us one,
+        # otherwise use the error's default message
+        error_opts[:_key] = opts[:error_key] if opts[:error_key]
+
+        # Raise the error, use the type the caller gave us or the comm default
         raise opts[:error_class], error_opts
       end
     end #WinRM class
diff --git a/plugins/communicators/winrm/errors.rb b/plugins/communicators/winrm/errors.rb
index 2285d2115..552b8a300 100644
--- a/plugins/communicators/winrm/errors.rb
+++ b/plugins/communicators/winrm/errors.rb
@@ -18,6 +18,10 @@ module VagrantPlugins
         error_key(:invalid_shell)
       end
 
+      class WinRMBadExitStatus < WinRMError
+        error_key(:winrm_bad_exit_status)
+      end
+
       class WinRMNotReady < WinRMError
         error_key(:winrm_not_ready)
       end
diff --git a/templates/locales/comm_winrm.yml b/templates/locales/comm_winrm.yml
index 0189547f9..9de47a9cf 100644
--- a/templates/locales/comm_winrm.yml
+++ b/templates/locales/comm_winrm.yml
@@ -8,6 +8,19 @@ en:
         Password: %{password}
         Endpoint: %{endpoint}
         Message: %{message}
+      winrm_bad_exit_status: |-
+        The following WinRM command responded with a non-zero exit status.
+        Vagrant assumes that this means the command failed!
+
+        %{command}
+
+        Stdout from the command:
+
+        %{stdout}
+
+        Stderr from the command:
+
+        %{stderr}
       execution_error: |-
         An error occurred executing a remote WinRM command.
 
diff --git a/test/unit/plugins/communicators/winrm/communicator_test.rb b/test/unit/plugins/communicators/winrm/communicator_test.rb
index 80d11d4c6..1433f4317 100644
--- a/test/unit/plugins/communicators/winrm/communicator_test.rb
+++ b/test/unit/plugins/communicators/winrm/communicator_test.rb
@@ -61,9 +61,10 @@ describe VagrantPlugins::CommunicatorWinRM::Communicator do
     end
 
     it "raises error when error_check is true and exit code is non-zero" do
-      expect(shell).to receive(:powershell).with(kind_of(String)).and_return({ exitcode: 1 })
+      expect(shell).to receive(:powershell).with(kind_of(String)).and_return(
+        { exitcode: 1, data: [{ stdout: '', stderr: '' }] })
       expect { subject.execute("dir") }.to raise_error(
-        VagrantPlugins::CommunicatorWinRM::Errors::ExecutionError)
+        VagrantPlugins::CommunicatorWinRM::Errors::WinRMBadExitStatus)
     end
 
     it "does not raise error when error_check is false and exit code is non-zero" do