diff --git a/sdk_lib/enter_chroot.sh b/sdk_lib/enter_chroot.sh
index 6683004832..86c7f6116d 100755
--- a/sdk_lib/enter_chroot.sh
+++ b/sdk_lib/enter_chroot.sh
@@ -261,13 +261,6 @@ setup_env() {
       disown $!
     fi
 
-    # Turn off automounting of external media when we enter the chroot by
-    # stopping the gvfs-gdu-volume-monitor and gvfsd-trash daemons. This is
-    # currently the most reliable way to disable automounting.
-    # See https://bugzilla.gnome.org/show_bug.cgi?id=677648
-    sudo killall -STOP -r '^gvfs-gdu-volume.*$|^gvfsd-trash$' 2>/dev/null \
-      || true
-
     debug "Mounting chroot environment."
     MOUNT_CACHE=$(echo $(awk '{print $2}' /proc/mounts))
     mount_queue_init
@@ -394,6 +387,22 @@ setup_env() {
         warn "-- Note: modprobe fuse failed.  gmergefs will not work"
     fi
 
+    # Turn off automounting of external media when we enter the
+    # chroot; thus we don't have to worry about being able to unmount
+    # from inside.
+    if SAVED_PREF=$(gconftool-2 -g ${AUTOMOUNT_PREF} 2>/dev/null); then
+      if [ "${SAVED_PREF}" != "false" ]; then
+        if [ $(gconftool-2 -s --type=boolean ${AUTOMOUNT_PREF} false) ]; then
+          warn "-- Note: USB sticks may be automounted by your host OS."
+          warn "-- Note: If you plan to burn bootable media, you may need to"
+          warn "-- Note: unmount these devices manually, or run image_to_usb.sh"
+          warn "-- Note: outside the chroot."
+        fi
+      fi
+    fi
+    # Always write the temp file so we can read it when exiting
+    echo "${SAVED_PREF:-false}" > "${FLAGS_chroot}${SAVED_AUTOMOUNT_PREF_FILE}"
+
     # Fix permissions on ccache tree.  If this is a fresh chroot, then they
     # might not be set up yet.  Or if the user manually `rm -rf`-ed things,
     # we need to reset it.  Otherwise, gcc itself takes care of fixing things
@@ -505,6 +514,12 @@ teardown_env() {
     # Remove any dups from lock file while installing new one
     sort -u -n "$TMP_LOCKFILE" > "$LOCKFILE"
 
+    SAVED_PREF=$(<"${FLAGS_chroot}${SAVED_AUTOMOUNT_PREF_FILE}")
+    if [ "${SAVED_PREF}" != "false" ]; then
+      gconftool-2 -s --type=boolean ${AUTOMOUNT_PREF} ${SAVED_PREF} || \
+        warn "could not re-set your automount preference."
+    fi
+
     if [ -s "$LOCKFILE" ]; then
       debug "At least one other pid is running in the chroot, so not"
       debug "tearing down env."
@@ -531,10 +546,6 @@ teardown_env() {
 
       debug "Unmounting chroot environment."
       safe_umount_tree "${MOUNTED_PATH}/"
-
-      # Now that we've exited the chroot, allow automounting again.
-      sudo killall -CONT -r '^gvfs-gdu-volume.*$|^gvfsd-trash$' 2>/dev/null \
-        || true
     fi
   ) 200>>"$LOCKFILE" || die "teardown_env failed"
 }
diff --git a/update_bootloaders.sh b/update_bootloaders.sh
index 5aa9b9326b..681f4935eb 100755
--- a/update_bootloaders.sh
+++ b/update_bootloaders.sh
@@ -161,16 +161,19 @@ fi
 
 ESP_FS_DIR=$(mktemp -d /tmp/esp.XXXXXX)
 cleanup() {
-  local failed=()
-  if [[ -n "${ESP_FS_DIR}" ]]; then
-    sudo umount "${ESP_FS_DIR}" && rm -rf "${ESP_FS_DIR}" || failed+=( umount )
+  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}"
   fi
   if [[ -n "${ESP_DEV}" && -z "${ESP_DEV//\/dev\/loop*}" ]]; then
-    sudo losetup -d "${ESP_DEV}" || failed+=( losetup )
-  fi
-  if [[ -n "${failed[*]}" ]]; then
-    die "Cleanup failed in ${failed[*]}"
+    sudo losetup -d  "${ESP_DEV}"
   fi
+  rm -rf "${ESP_FS_DIR}"
 }
 trap cleanup EXIT
 sudo mount "${ESP_DEV}" "${ESP_FS_DIR}"
@@ -212,9 +215,9 @@ if [[ "${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