diff --git a/cmd/cloudflared/updater/update.go b/cmd/cloudflared/updater/update.go
index 5ad40dcb..31be284f 100644
--- a/cmd/cloudflared/updater/update.go
+++ b/cmd/cloudflared/updater/update.go
@@ -6,6 +6,7 @@ import (
 	"os"
 	"path/filepath"
 	"runtime"
+	"strings"
 	"time"
 
 	"github.com/facebookgo/grace/gracenet"
@@ -95,11 +96,24 @@ func CheckForUpdate(options updateOptions) (CheckResult, error) {
 		url = StagingUpdateURL
 	}
 
+	if runtime.GOOS == "windows" {
+		cfdPath = encodeWindowsPath(cfdPath)
+	}
+
 	s := NewWorkersService(version, url, cfdPath, Options{IsBeta: options.isBeta,
 		IsForced: options.isForced, RequestedVersion: options.intendedVersion})
 
 	return s.Check()
 }
+func encodeWindowsPath(path string) string {
+	// We do this because Windows allows spaces in directories such as
+	// Program Files but does not allow these directories to be spaced in batch files.
+	targetPath := strings.Replace(path, "Program Files (x86)", "PROGRA~2", -1)
+	// This is to do the same in 32 bit systems. We do this second so that the first
+	// replace is for x86 dirs.
+	targetPath = strings.Replace(targetPath, "Program Files", "PROGRA~1", -1)
+	return targetPath
+}
 
 func applyUpdate(options updateOptions, update CheckResult) UpdateOutcome {
 	if update.Version() == "" || options.updateDisabled {
diff --git a/cmd/cloudflared/updater/workers_update.go b/cmd/cloudflared/updater/workers_update.go
index 443f896d..b2d451a9 100644
--- a/cmd/cloudflared/updater/workers_update.go
+++ b/cmd/cloudflared/updater/workers_update.go
@@ -25,14 +25,13 @@ const (
 	// rename cloudflared.exe.new to cloudflared.exe
 	// delete cloudflared.exe.old
 	// start the service
-	// delete the batch file
-	windowsUpdateCommandTemplate = `@echo off
-sc stop cloudflared >nul 2>&1
+	// exit with code 0 if we've reached this point indicating success.
+	windowsUpdateCommandTemplate = `sc stop cloudflared >nul 2>&1
 rename "{{.TargetPath}}" {{.OldName}}
 rename "{{.NewPath}}" {{.BinaryName}}
 del "{{.OldPath}}"
 sc start cloudflared >nul 2>&1
-del {{.BatchName}}`
+exit /b 0`
 	batchFileName = "cfd_update.bat"
 )
 
@@ -214,8 +213,9 @@ func isValidChecksum(checksum, filePath string) error {
 // writeBatchFile writes a batch file out to disk
 // see the dicussion on why it has to be done this way
 func writeBatchFile(targetPath string, newPath string, oldPath string) error {
-	os.Remove(batchFileName) //remove any failed updates before download
-	f, err := os.Create(batchFileName)
+	batchFilePath := filepath.Join(filepath.Dir(targetPath), batchFileName)
+	os.Remove(batchFilePath) //remove any failed updates before download
+	f, err := os.Create(batchFilePath)
 	if err != nil {
 		return err
 	}
@@ -241,6 +241,16 @@ func writeBatchFile(targetPath string, newPath string, oldPath string) error {
 
 // run each OS command for windows
 func runWindowsBatch(batchFile string) error {
-	cmd := exec.Command("cmd", "/c", batchFile)
-	return cmd.Start()
+	defer os.Remove(batchFile)
+	cmd := exec.Command("cmd", "/C", batchFile)
+	_, err := cmd.Output()
+	// Remove the batch file we created. Don't let this interfere with the error
+	// we report.
+	if err != nil {
+		if exitError, ok := err.(*exec.ExitError); ok {
+			return fmt.Errorf("Error during update : %s;", string(exitError.Stderr))
+		}
+
+	}
+	return err
 }