diff --git a/update_bootloaders.sh b/update_bootloaders.sh
index 1f6bbd9ec1..5aa9b9326b 100755
--- a/update_bootloaders.sh
+++ b/update_bootloaders.sh
@@ -1,6 +1,6 @@
 #!/bin/bash
 
-# Copyright (c) 2010 The Chromium OS Authors. All rights reserved.
+# Copyright (c) 2012 The Chromium OS Authors. All rights reserved.
 # Use of this source code is governed by a BSD-style license that can be
 # found in the LICENSE file.
 
@@ -161,19 +161,16 @@ fi
 
 ESP_FS_DIR=$(mktemp -d /tmp/esp.XXXXXX)
 cleanup() {
-  set +e
-  if ! sudo umount "${ESP_FS_DIR}"; then
-      # There is a race condition possible on some ubuntu setups
-      # with mounting and unmounting a device very quickly
-      # Doing a quick sleep/retry as a temporary workaround
-      warn "Initial unmount failed. Possibly crosbug.com/23443. Retrying"
-      sleep 5
-      sudo umount "${ESP_FS_DIR}"
+  local failed=()
+  if [[ -n "${ESP_FS_DIR}" ]]; then
+    sudo umount "${ESP_FS_DIR}" && rm -rf "${ESP_FS_DIR}" || failed+=( umount )
   fi
   if [[ -n "${ESP_DEV}" && -z "${ESP_DEV//\/dev\/loop*}" ]]; then
-    sudo losetup -d  "${ESP_DEV}"
+    sudo losetup -d "${ESP_DEV}" || failed+=( losetup )
+  fi
+  if [[ -n "${failed[*]}" ]]; then
+    die "Cleanup failed in ${failed[*]}"
   fi
-  rm -rf "${ESP_FS_DIR}"
 }
 trap cleanup EXIT
 sudo mount "${ESP_DEV}" "${ESP_FS_DIR}"
@@ -215,9 +212,9 @@ if [[ "${FLAGS_arch}" = "x86" || "${FLAGS_arch}" = "amd64" ]]; then
   # we cut over from rootfs booting (extlinux).
   if [[ ${FLAGS_install_syslinux} -eq ${FLAGS_TRUE} ]]; then
     sudo umount "${ESP_FS_DIR}"
+    rm -rf "${ESP_FS_DIR}"
+    ESP_FS_DIR=
     sudo syslinux -d /syslinux "${ESP_DEV}"
-    # mount again for cleanup to free resource gracefully
-    sudo mount -o ro "${ESP_DEV}" "${ESP_FS_DIR}"
   fi
 elif [[ "${FLAGS_arch}" = "arm" ]]; then
   # Copy u-boot script to ESP partition