diff --git a/pkg/crc/preflight/preflight_checks_tray_windows.go b/pkg/crc/preflight/preflight_checks_tray_windows.go
index 494151752a..8bc481cff9 100644
--- a/pkg/crc/preflight/preflight_checks_tray_windows.go
+++ b/pkg/crc/preflight/preflight_checks_tray_windows.go
@@ -4,95 +4,145 @@ import (
 	"fmt"
 	"io/ioutil"
 	goos "os"
-	"os/exec"
-	"os/user"
 	"path/filepath"
 	"strings"
+	"time"
 
 	"github.com/code-ready/crc/pkg/crc/constants"
 	"github.com/code-ready/crc/pkg/crc/input"
 	"github.com/code-ready/crc/pkg/crc/logging"
-	"github.com/code-ready/crc/pkg/crc/version"
 	dl "github.com/code-ready/crc/pkg/download"
 	"github.com/code-ready/crc/pkg/embed"
 	"github.com/code-ready/crc/pkg/extract"
 	"github.com/code-ready/crc/pkg/os"
 	"github.com/code-ready/crc/pkg/os/windows/powershell"
-	"github.com/code-ready/crc/pkg/os/windows/secpol"
-	"github.com/code-ready/crc/pkg/os/windows/service"
 )
 
-var (
-	startUpFolder   = filepath.Join(constants.GetHomeDir(), "AppData", "Roaming", "Microsoft", "Windows", "Start Menu", "Programs", "Startup")
-	trayProcessName = constants.TrayBinaryName[:len(constants.TrayBinaryName)-4]
-)
+func checkIfTrayInstalled() error {
+	/* We want to force installation whenever setup is ran
+	 * as we want the service config to point to the binary
+	 * with which the setup command was issued.
+	 */
 
-func checkIfDaemonServiceInstalled() error {
-	// We want to force installation whenever setup is ran
-	// as we want the service config to point to the binary
-	// with which the setup command was issued
-	return fmt.Errorf("Ignoring check and forcing installation of daemon service")
+	return fmt.Errorf("Ignoring check and forcing installation of System Tray")
 }
 
-func fixDaemonServiceInstalled() error {
-	// only try to remove if a previous version exists
-	if service.IsInstalled(constants.DaemonServiceName) {
-		if service.IsRunning(constants.DaemonServiceName) {
-			_ = service.Stop(constants.DaemonServiceName)
-		}
-		_ = service.Delete(constants.DaemonServiceName)
+func fixTrayInstalled() error {
+	/* To avoid asking for elevated privileges again and again
+	 * this takes care of all the steps needed to have a running
+	 * tray by invoking a ps script which does the following:
+	 * a) Add logon as service permission for the user
+	 * b) Create the daemon service and start it
+	 * c) Add tray to startup folder and start it
+	 */
+
+	tempDir, err := ioutil.TempDir("", "crc")
+	if err != nil {
+		logging.Error("Failed creating temporary directory for tray installation")
+		return err
 	}
 
-	// get executables path
+	defer func() {
+		_ = goos.RemoveAll(tempDir)
+	}()
+
+	// prepare the ps script
 	binPath, err := goos.Executable()
 	if err != nil {
 		return fmt.Errorf("Unable to find the current executables location: %v", err)
 	}
 	binPathWithArgs := fmt.Sprintf("%s daemon", strings.TrimSpace(binPath))
 
-	// get the account name
-	u, err := user.Current()
-	if err != nil {
-		return fmt.Errorf("Failed to get username: %v", err)
-	}
-	logging.Debug("Got username: ", u.Username)
-	accountName := strings.TrimSpace(u.Username)
-
 	// get the password from user
 	password, err := input.PromptUserForSecret("Enter account login password for service installation", "This is the login password of your current account, needed to install the daemon service")
 	if err != nil {
 		return fmt.Errorf("Unable to get login password: %v", err)
 	}
-	err = service.Create(constants.DaemonServiceName, binPathWithArgs, accountName, password)
+
+	// sanitize password
+	password = escapeWindowsPassword(password)
+
+	psScriptContent := genTrayInstallScript(
+		password,
+		tempDir,
+		binPathWithArgs,
+		constants.TrayBinaryPath,
+		constants.TrayShortcutName,
+		constants.DaemonServiceName,
+	)
+	psFilePath := filepath.Join(tempDir, "trayInstallation.ps1")
+
+	// write temporary ps script
+	if err = writePsScriptContentToFile(psScriptContent, psFilePath); err != nil {
+		return err
+	}
+
+	// invoke the ps script
+	_, _, err = powershell.ExecuteAsAdmin("Installing System Tray for CodeReady Containers", psFilePath)
+	// wait for the script to finish executing
+	time.Sleep(2 * time.Second)
 	if err != nil {
-		return fmt.Errorf("Failed to install CodeReady Containers daemon service: %v", err)
+		logging.Debug("Failed to execute tray installation script")
+		return err
+	}
+
+	// check for 'success' file
+	if _, err = goos.Stat(filepath.Join(tempDir, "success")); goos.IsNotExist(err) {
+		return fmt.Errorf("Installation script didn't execute successfully: %v", err)
 	}
 	return nil
 }
 
-func removeDaemonService() error {
-	// try to remove service if only it is installed
-	// this should remove unnecessary UAC prompts during cleanup
-	// service.IsInstalled doesn't need an admin shell to run
-	if service.IsInstalled(constants.DaemonServiceName) {
-		err := service.Stop(constants.DaemonServiceName)
-		if err != nil {
-			return fmt.Errorf("Failed to stop the daemon service: %v", err)
-		}
-		return service.Delete(constants.DaemonServiceName)
+func escapeWindowsPassword(password string) string {
+	// escape specials characters (|`|$|"|') with '`' if present in password
+	if strings.Contains(password, "`") {
+		password = strings.Replace(password, "`", "``", -1)
 	}
-	return nil
+	if strings.Contains(password, "$") {
+		password = strings.Replace(password, "$", "`$", -1)
+	}
+	if strings.Contains(password, "\"") {
+		password = strings.Replace(password, "\"", "`\"", -1)
+	}
+	if strings.Contains(password, "'") {
+		password = strings.Replace(password, "'", "`'", -1)
+	}
+	return password
 }
 
-func checkIfDaemonServiceRunning() error {
-	if service.IsRunning(constants.DaemonServiceName) {
+func removeTray() error {
+	trayProcessName := constants.TrayBinaryName[:len(constants.TrayBinaryName)-4]
+
+	tempDir, err := ioutil.TempDir("", "crc")
+	if err != nil {
+		logging.Debug("Failed to create temporary directory for System Tray removal")
+		return nil
+	}
+	defer func() {
+		_ = goos.RemoveAll(tempDir)
+	}()
+
+	psScriptContent := genTrayRemovalScript(
+		trayProcessName,
+		constants.TrayShortcutName,
+		constants.DaemonServiceName,
+		tempDir,
+	)
+	psFilePath := filepath.Join(tempDir, "trayRemoval.ps1")
+
+	// write script content to temporary file
+	if err = writePsScriptContentToFile(psScriptContent, psFilePath); err != nil {
+		logging.Debug(err)
 		return nil
 	}
-	return fmt.Errorf("CodeReady Containers dameon service is not running")
-}
 
-func fixDaemonServiceRunning() error {
-	return service.Start(constants.DaemonServiceName)
+	_, _, err = powershell.ExecuteAsAdmin("Uninstalling CodeReady Containers System Tray", psFilePath)
+	// wait for the script to finish executing
+	time.Sleep(2 * time.Second)
+	if err != nil {
+		logging.Debugf("Unable to execute System Tray uninstall script: %v", err)
+	}
+	return nil
 }
 
 func checkTrayBinaryExists() error {
@@ -131,123 +181,27 @@ func fixTrayBinaryExists() error {
 	return nil
 }
 
-func checkTrayBinaryVersion() error {
-	versionCmd := `(Get-Item %s).VersionInfo.ProductVersion`
-	stdOut, stdErr, err := powershell.Execute(fmt.Sprintf(versionCmd, constants.TrayBinaryPath))
-	if err != nil {
-		return fmt.Errorf("Failed to get the version of tray: %v: %s", err, stdErr)
-	}
-	currentTrayVersion := strings.TrimSpace(stdOut)
-	if currentTrayVersion != version.GetCRCWindowsTrayVersion() {
-		return fmt.Errorf("Current tray version doesn't match with expected version")
-	}
-	return nil
-}
-
-func fixTrayBinaryVersion() error {
-	// If a tray is already running kill it
-	if err := checkTrayRunning(); err == nil {
-		cmd := `Stop-Process -Name "tray-windows"`
-		if _, _, err := powershell.Execute(cmd); err != nil {
-			logging.Debugf("Failed to kill running tray: %v", err)
-		}
-	}
-	return fixTrayBinaryExists()
-}
-
-func checkTrayBinaryAddedToStartupFolder() error {
-	if os.FileExists(filepath.Join(startUpFolder, constants.TrayShortcutName)) {
-		return nil
-	}
-	return fmt.Errorf("Tray shortcut does not exists in startup folder")
-}
-
-func fixTrayBinaryAddedToStartupFolder() error {
-	cmd := fmt.Sprintf(
-		"New-Item -ItemType SymbolicLink -Path \"%s\" -Name \"%s\" -Value \"%s\"",
-		startUpFolder,
-		constants.TrayShortcutName,
-		constants.TrayBinaryPath,
-	)
-	_, _, err := powershell.ExecuteAsAdmin("Adding tray binary to startup applications", cmd)
-	if err != nil {
-		return fmt.Errorf("Failed to create shortcut of tray binary in startup folder: %v", err)
-	}
-	return nil
-}
-
-func removeTrayBinaryFromStartupFolder() error {
-	err := goos.Remove(filepath.Join(startUpFolder, constants.TrayShortcutName))
-	if err != nil {
-		logging.Warn("Failed to remove tray from startup folder: ", err)
-	}
-	return nil
-}
-
-func checkTrayRunning() error {
-	cmd := fmt.Sprintf("Get-Process -Name \"%s\"", trayProcessName)
-	_, stdErr, err := powershell.Execute(cmd)
-	if err != nil {
-		return fmt.Errorf("Failed to check if the tray is running: %v", err)
-	}
-	if strings.Contains(stdErr, constants.TrayBinaryName) {
-		return fmt.Errorf("Tray binary is not running")
-	}
-	return nil
-}
-
-func fixTrayRunning() error {
-	// #nosec G204
-	err := exec.Command(constants.TrayBinaryPath).Start()
+func writePsScriptContentToFile(psScriptContent, psFilePath string) error {
+	psFile, err := goos.Create(psFilePath)
 	if err != nil {
+		logging.Debugf("Unable to create file to write scipt content: %v", err)
 		return err
 	}
-	return nil
-}
-
-func stopTray() error {
-	if err := checkTrayRunning(); err != nil {
-		logging.Debug("Failed to check if a tray is running: ", err)
-		return nil
-	}
-	cmd := fmt.Sprintf("Stop-Process -Name %s", trayProcessName)
-	_, _, err := powershell.Execute(cmd)
+	defer psFile.Close()
+	// write the ps script
+	/* Add UTF-8 BOM at the beginning of the script so that Windows
+	 * correctly detects the file encoding
+	 */
+	_, err = psFile.Write([]byte{0xef, 0xbb, 0xbf})
 	if err != nil {
-		logging.Warn("Failed to stop running tray: ", err)
-	}
-	return nil
-}
-
-func checkUserHasServiceLogonEnabled() error {
-	username := getCurrentUsername()
-	enabled, err := secpol.UserAllowedToLogonAsService(username)
-	if enabled {
-		return nil
+		logging.Debugf("Unable to write script content to file: %v", err)
+		return err
 	}
-	return fmt.Errorf("Failed to check if user is allowed to log on as service: %v", err)
-}
-
-func fixUserHasServiceLogonEnabled() error {
-	// get the username
-	username := getCurrentUsername()
-
-	return secpol.AllowUserToLogonAsService(username)
-}
-
-func getCurrentUsername() string {
-	user, err := user.Current()
+	_, err = psFile.WriteString(psScriptContent)
 	if err != nil {
-		logging.Debugf("Unable to get current user's name: %v", err)
-		return ""
+		logging.Debugf("Unable to write script content to file: %v", err)
+		return err
 	}
-	return strings.TrimSpace(strings.Split(user.Username, "\\")[1])
-}
-
-func disableUserServiceLogon() error {
-	username := getCurrentUsername()
 
-	if err := secpol.RemoveLogonAsServiceUserRight(username); err != nil {
-		logging.Warn("Failed trying to remove log on as a service user right: ", err)
-	}
 	return nil
 }
diff --git a/pkg/crc/preflight/preflight_checks_tray_windows_test.go b/pkg/crc/preflight/preflight_checks_tray_windows_test.go
new file mode 100644
index 0000000000..2f800383a6
--- /dev/null
+++ b/pkg/crc/preflight/preflight_checks_tray_windows_test.go
@@ -0,0 +1,29 @@
+package preflight
+
+import (
+	"fmt"
+	"strings"
+	"testing"
+
+	"github.com/code-ready/crc/pkg/os/windows/powershell"
+)
+
+func TestEscapeWindowsPassword(t *testing.T) {
+	passwords := []string{
+		"tes;t@\"_\\/",
+		"$kdhhjs;%&*'`",
+		"``````$''\"",
+	}
+
+	for _, pass := range passwords {
+		op := escapeWindowsPassword(pass)
+		psCmd := fmt.Sprintf("$var=\"%s\"; $var", op)
+		stdOut, stdErr, err := powershell.Execute(psCmd)
+		if err != nil {
+			t.Errorf("Error while executing powershell command: %v: %v", err, stdErr)
+		}
+		if strings.TrimSpace(stdOut) != pass {
+			t.Errorf("Passwords don't match after escaping for powershell. Expected: %s, Actual: %s", pass, stdOut)
+		}
+	}
+}
diff --git a/pkg/crc/preflight/preflight_tray_powershell_windows.go b/pkg/crc/preflight/preflight_tray_powershell_windows.go
new file mode 100644
index 0000000000..248b5f6c90
--- /dev/null
+++ b/pkg/crc/preflight/preflight_tray_powershell_windows.go
@@ -0,0 +1,170 @@
+package preflight
+
+import (
+	"fmt"
+	"strings"
+)
+
+var (
+	trayInstallationScript = []string{
+		`$ErrorActionPreference = "Stop"`,
+		`$password = "%s"`,
+		`$tempDir = "%s"`,
+		`$crcBinaryPath = "%s"`,
+		`$trayBinaryPath = "%s"`,
+		`$traySymlinkName = "%s"`,
+		`$serviceName = "%s"`,
+		`$currentUserSid = (Get-LocalUser -Name "$env:USERNAME").Sid.Value`,
+		`$startUpFolder = "$Env:USERPROFILE\AppData\Roaming\Microsoft\Windows\Start Menu\Programs\Startup"`,
+		`function AddServiceLogonRightForCurrentUser()`,
+		`{`,
+		`	$securityTemplate = @"`,
+		`[Unicode]`,
+		`Unicode=yes`,
+		`[Version]`,
+		"signature=\"`$CHICAGO$\"",
+		`Revision=1`,
+		`[Privilege Rights]`,
+		`SeServiceLogonRight = {0}`,
+		`"@`,
+		`	SecEdit.exe /export /cfg $tempDir\secdef.inf /areas USER_RIGHTS`,
+		`	if ($LASTEXITCODE -ne 0)`,
+		`	{`,
+		`		exit 1`,
+		`	}`,
+		`	$userRights = Get-Content -Path $tempDir\secdef.inf`,
+		`	$serviceLogonUserRight = ($userRights | select-string -Pattern "SeServiceLogonRight\s=\s.*")`,
+		`	$sidsInServiceLogonRight = ($serviceLogonUserRight -split "=")[1].Trim()`,
+		`	$sidsArray = $sidsInServiceLogonRight -split ","`,
+		`	if (!($sidsArray.Contains($env:USERNAME) -or $sidsArray.Contains("*"+$currentUserSid)))`,
+		`	{`,
+		`		Write-Output "User doesn't have logon as service right, adding sid of $env:Username"`,
+		`		$sidsInServiceLogonRight += ",*$currentUserSid"`,
+		`		$templateContent = $securityTemplate -f "$sidsInServiceLogonRight"`,
+		`		Set-Content -Path $tempDir\secdef_fin.inf $templateContent`,
+		`		SecEdit.exe /configure /db $tempDir\tempdb.db /cfg $tempDir\secdef_fin.inf /areas USER_RIGHTS`,
+		`		if ($LASTEXITCODE -ne 0)`,
+		`		{`,
+		`			exit`,
+		`		}`,
+		`	}`,
+		`}`,
+
+		`function CreateDaemonService()`,
+		`{`,
+		`	$secPass = ConvertTo-SecureString $password -AsPlainText -Force`,
+		`	$creds = New-Object pscredential ("$env:USERDOMAIN\$env:USERNAME", $secPass)`,
+		`	$params = @{`,
+		`		Name = "$serviceName"`,
+		`		BinaryPathName = "$crcBinaryPath daemon"`,
+		`		DisplayName = "$serviceName"`,
+		`		StartupType = "Automatic"`,
+		`		Description = "CodeReady Containers Daemon service for System Tray."`,
+		`		Credential = $creds`,
+		`	}`,
+		`	New-Service @params`,
+		`}`,
+
+		`function StartDaemonService()`,
+		`{`,
+		`	Start-Service "CodeReady Containers"`,
+		`}`,
+
+		`AddServiceLogonRightForCurrentUser`,
+		`sc.exe stop "$serviceName"`,
+		`sc.exe delete "$serviceName"`,
+		`CreateDaemonService`,
+		`StartDaemonService`,
+		`$ErrorActionPreference = "Continue"`,
+		`Stop-Process -Name tray-windows`,
+		`Remove-Item "$startUpFolder\$traySymlinkName"`,
+
+		`$ErrorActionPreference = "Stop"`,
+		`New-Item -ItemType SymbolicLink -Path "$startUpFolder" -Name "$traySymlinkName" -Value "$trayBinaryPath"`,
+		`Start-Process -FilePath "$trayBinaryPath"`,
+		`New-Item -ItemType File -Path "$tempDir" -Name "success"`,
+		`Set-Content -Path $tempDir\success "blah blah"`,
+	}
+
+	trayRemovalScript = []string{
+		`$tempDir = "%s"`,
+		`$trayProcessName = "%s"`,
+		`$traySymlinkName = "%s"`,
+		`$serviceName = "%s"`,
+		`$startUpFolder = "$Env:USERPROFILE\AppData\Roaming\Microsoft\Windows\Start Menu\Programs\Startup"`,
+
+		`function RemoveUserFromServiceLogon`,
+		`{`,
+		`	$securityTemplate = @"`,
+		`[Unicode]`,
+		`Unicode=yes`,
+		`[Version]`,
+		"signature=\"`$CHICAGO$\"",
+		`Revision=1`,
+		`[Privilege Rights]`,
+		`SeServiceLogonRight = {0}`,
+		`"@`,
+		`	SecEdit.exe /export /cfg $tempDir\secdef.inf /areas USER_RIGHTS`,
+		`	if ($LASTEXITCODE -ne 0)`,
+		`	{`,
+		`		exit 1`,
+		`	}`,
+
+		`	$userRights = Get-Content -Path $tempDir\secdef.inf`,
+		`	$serviceLogonUserRight = ($userRights | select-string -Pattern "SeServiceLogonRight\s=\s.*")`,
+
+		`	$sidsInServiceLogonRight = ($serviceLogonUserRight -split "=")[1].Trim()`,
+		`	$sidsArray = $sidsInServiceLogonRight -split ","`,
+		`	$newSids = $sidsArray | Where-Object {$_ -ne $env:USERNAME}`,
+		`	$newSids = $newSids -Join ","`,
+		`	$templateContent = $securityTemplate -f "$newSids"`,
+
+		`	Set-Content -Path $tempDir\secdef_fin.inf $templateContent`,
+		`	SecEdit.exe /configure /db $tempDir\tempdb.db /cfg $tempDir\secdef_fin.inf /areas USER_RIGHTS`,
+		`}`,
+
+		`function DeleteDaemonService()`,
+		`{`,
+		`	sc.exe stop "$serviceName"`,
+		`	sc.exe delete "$serviceName"`,
+		`}`,
+
+		`function RemoveTrayFromStartUpFolder()`,
+		`{`,
+		`	Stop-Process -Name "$trayProcessName"`,
+		`	Remove-Item "$startUpFolder\$traySymlinkName"`,
+		`}`,
+
+		`RemoveUserFromServiceLogon`,
+		`DeleteDaemonService`,
+		`RemoveTrayFromStartUpFolder`,
+	}
+)
+
+func getTrayInstallationScriptTemplate() string {
+	return strings.Join(trayInstallationScript, "\n")
+}
+
+func getTrayRemovalScriptTemplate() string {
+	return strings.Join(trayRemovalScript, "\n")
+}
+
+func genTrayInstallScript(password, tempDirPath, daemonCmd, trayBinaryPath, traySymlinkName, daemonServiceName string) string {
+	return fmt.Sprintf(getTrayInstallationScriptTemplate(),
+		password,
+		tempDirPath,
+		daemonCmd,
+		trayBinaryPath,
+		traySymlinkName,
+		daemonServiceName,
+	)
+}
+
+func genTrayRemovalScript(trayProcessName, traySymlinkName, daemonServiceName, tempDir string) string {
+	return fmt.Sprintf(getTrayRemovalScriptTemplate(),
+		tempDir,
+		trayProcessName,
+		traySymlinkName,
+		daemonServiceName,
+	)
+}
diff --git a/pkg/crc/preflight/preflight_windows.go b/pkg/crc/preflight/preflight_windows.go
index ddc4fe9ce9..d8154ba451 100644
--- a/pkg/crc/preflight/preflight_windows.go
+++ b/pkg/crc/preflight/preflight_windows.go
@@ -56,31 +56,6 @@ var hypervPreflightChecks = [...]Check{
 }
 
 var traySetupChecks = [...]Check{
-	{
-		checkDescription:   "Checking if user is allowed to log on as a service",
-		check:              checkUserHasServiceLogonEnabled,
-		fixDescription:     "Enabling service log on for user",
-		fix:                fixUserHasServiceLogonEnabled,
-		cleanupDescription: "Removing service log on permission from user",
-		cleanup:            disableUserServiceLogon,
-		flags:              SetupOnly,
-	},
-	{
-		checkDescription:   "Checking if daemon service is installed",
-		check:              checkIfDaemonServiceInstalled,
-		fixDescription:     "Installing daemon service",
-		fix:                fixDaemonServiceInstalled,
-		cleanupDescription: "Removing daemon service if exists",
-		cleanup:            removeDaemonService,
-		flags:              SetupOnly,
-	},
-	{
-		checkDescription: "Checking if daemon service is running",
-		check:            checkIfDaemonServiceRunning,
-		fixDescription:   "Starting daemon service",
-		fix:              fixDaemonServiceRunning,
-		flags:            SetupOnly,
-	},
 	{
 		checkDescription: "Checking if tray binary is present",
 		check:            checkTrayBinaryExists,
@@ -89,28 +64,12 @@ var traySetupChecks = [...]Check{
 		flags:            SetupOnly,
 	},
 	{
-		checkDescription:   "Checking if tray binary is added to startup applications",
-		check:              checkTrayBinaryAddedToStartupFolder,
-		fixDescription:     "Adding tray binary to startup applications",
-		fix:                fixTrayBinaryAddedToStartupFolder,
-		cleanupDescription: "Removing tray binary from startup folder if exists",
-		cleanup:            removeTrayBinaryFromStartupFolder,
-		flags:              SetupOnly,
-	},
-	{
-		checkDescription: "Checking if tray version is correct",
-		check:            checkTrayBinaryVersion,
-		fixDescription:   "Caching correct tray version",
-		fix:              fixTrayBinaryVersion,
-		flags:            SetupOnly,
-	},
-	{
-		checkDescription:   "Checking if tray is running",
-		check:              checkTrayRunning,
-		fixDescription:     "Starting CodeReady Containers tray",
-		fix:                fixTrayRunning,
-		cleanupDescription: "Stopping tray process if running",
-		cleanup:            stopTray,
+		checkDescription:   "Checking if tray is installed",
+		check:              checkIfTrayInstalled,
+		fixDescription:     "Installing CodeReady Containers tray",
+		fix:                fixTrayInstalled,
+		cleanupDescription: "Uninstalling tray if installed",
+		cleanup:            removeTray,
 		flags:              SetupOnly,
 	},
 }