diff --git a/communicator/winrm/communicator.go b/communicator/winrm/communicator.go
index 548abe9f5..1e543dceb 100644
--- a/communicator/winrm/communicator.go
+++ b/communicator/winrm/communicator.go
@@ -130,7 +130,11 @@ func (c *Communicator) Upload(path string, input io.Reader, fi *os.FileInfo) err
 	}
 	if strings.HasSuffix(path, `\`) {
 		// path is a directory
-		path += filepath.Base((*fi).Name())
+		if fi != nil {
+			path += filepath.Base((*fi).Name())
+		} else {
+			return fmt.Errorf("Was unable to infer file basename for upload.")
+		}
 	}
 	log.Printf("Uploading file to '%s'", path)
 	return wcp.Write(path, input)
diff --git a/communicator/winrm/communicator_test.go b/communicator/winrm/communicator_test.go
index 3f650a000..b7bc78304 100644
--- a/communicator/winrm/communicator_test.go
+++ b/communicator/winrm/communicator_test.go
@@ -120,5 +120,25 @@ func TestUpload(t *testing.T) {
 	if downloadedPayload != PAYLOAD {
 		t.Fatalf("files are not equal: expected [%s] length: %v, got [%s] length %v", PAYLOAD, len(PAYLOAD), downloadedPayload, len(downloadedPayload))
 	}
+}
+
+func TestUpload_nilFileInfo(t *testing.T) {
+	wrm := newMockWinRMServer(t)
+	defer wrm.Close()
 
+	c, err := New(&Config{
+		Host:     wrm.Host,
+		Port:     wrm.Port,
+		Username: "user",
+		Password: "pass",
+		Timeout:  30 * time.Second,
+	})
+	if err != nil {
+		t.Fatalf("error creating communicator: %s", err)
+	}
+	file := "C:\\Temp\\"
+	err = c.Upload(file, strings.NewReader(PAYLOAD), nil)
+	if err == nil {
+		t.Fatalf("Should have errored because of nil fileinfo")
+	}
 }
diff --git a/provisioner/powershell/provisioner.go b/provisioner/powershell/provisioner.go
index b554ca6f2..6b0038947 100644
--- a/provisioner/powershell/provisioner.go
+++ b/provisioner/powershell/provisioner.go
@@ -9,6 +9,7 @@ import (
 	"fmt"
 	"log"
 	"os"
+	"path/filepath"
 	"sort"
 	"strings"
 	"time"
@@ -252,6 +253,14 @@ func (p *Provisioner) Provision(ctx context.Context, ui packer.Ui, comm packer.C
 		ui.Say(fmt.Sprintf("Provisioning with powershell script: %s", path))
 
 		log.Printf("Opening %s for reading", path)
+		fi, err := os.Stat(path)
+		if err != nil {
+			return fmt.Errorf("Error stating powershell script: %s", err)
+		}
+		if strings.HasSuffix(p.config.RemotePath, `\`) {
+			// path is a directory
+			p.config.RemotePath += filepath.Base((fi).Name())
+		}
 		f, err := os.Open(path)
 		if err != nil {
 			return fmt.Errorf("Error opening powershell script: %s", err)
@@ -272,7 +281,7 @@ func (p *Provisioner) Provision(ctx context.Context, ui packer.Ui, comm packer.C
 			if _, err := f.Seek(0, 0); err != nil {
 				return err
 			}
-			if err := comm.Upload(p.config.RemotePath, f, nil); err != nil {
+			if err := comm.Upload(p.config.RemotePath, f, &fi); err != nil {
 				return fmt.Errorf("Error uploading script: %s", err)
 			}