diff --git a/packer/communicator_mock.go b/packer/communicator_mock.go
index a0563f302..00b043a91 100644
--- a/packer/communicator_mock.go
+++ b/packer/communicator_mock.go
@@ -3,6 +3,7 @@ package packer
 import (
 	"bytes"
 	"context"
+	"errors"
 	"io"
 	"os"
 	"strings"
@@ -112,3 +113,19 @@ func (c *MockCommunicator) DownloadDir(src string, dst string, excl []string) er
 
 	return nil
 }
+
+// ScriptUploadErrorMockCommunicator returns an error from it's Upload() method
+// when a script is uploaded to test the case where this upload fails.
+type ScriptUploadErrorMockCommunicator struct {
+	MockCommunicator
+}
+
+var ScriptUploadErrorMockCommunicatorError = errors.New("ScriptUploadErrorMockCommunicator Upload error")
+
+func (c *ScriptUploadErrorMockCommunicator) Upload(path string, r io.Reader, fi *os.FileInfo) error {
+	// only fail on script uploads, not on environment variable uploads
+	if !strings.Contains(path, "packer-ps-env-vars") {
+		return ScriptUploadErrorMockCommunicatorError
+	}
+	return c.MockCommunicator.Upload(path, r, fi)
+}
diff --git a/provisioner/powershell/provisioner_test.go b/provisioner/powershell/provisioner_test.go
index 8d48fa2ee..c90d90f2e 100644
--- a/provisioner/powershell/provisioner_test.go
+++ b/provisioner/powershell/provisioner_test.go
@@ -8,6 +8,7 @@ import (
 	"regexp"
 	"strings"
 	"testing"
+	"time"
 
 	"github.com/hashicorp/packer/packer"
 )
@@ -502,6 +503,22 @@ func TestProvisionerProvision_UISlurp(t *testing.T) {
 	// UI should receive following messages / output
 }
 
+func TestProvisionerProvision_UploadFails(t *testing.T) {
+	config := testConfig()
+	ui := testUi()
+
+	p := new(Provisioner)
+	comm := new(packer.ScriptUploadErrorMockCommunicator)
+	p.Prepare(config)
+	p.config.StartRetryTimeout = time.Second
+	err := p.Provision(context.Background(), ui, comm)
+	if !strings.Contains(err.Error(), packer.ScriptUploadErrorMockCommunicatorError.Error()) {
+		t.Fatalf("expected Provision() error %q to contain %q",
+			err.Error(),
+			packer.ScriptUploadErrorMockCommunicatorError.Error())
+	}
+}
+
 func TestProvisioner_createFlattenedElevatedEnvVars_windows(t *testing.T) {
 	var flattenedEnvVars string
 	config := testConfig()