--- Please enter the report below this line. ---

upgraded all my packages after the freeze and grub doesn't boot anymore.
the error message is "error: file not found" and then it drops into the grub rescue console.

i fixed it by chrooting via a live cd and running "dpkg-reconfigure grub-pc"
(telling it to install to /dev/sda and /dev/sdb). works fine since then.

my hard drives are setup like this:
/dev/sda1 and /dev/sdb1 -> 500 MB /boot partition with software RAID1
/dev/sda5 and /dev/sdb5 -> root partition with software RAID1

further / has luks encryption and after that LVM with one PV for / (all setup with the debian installer)

let me know if you need more info. here's what i found from the log files before upgrading grub:

-----------------------

/var/log/messages:

May 23 19:37:57 dsteiner3 os-prober: debug: /dev/sda1: part of software raid array
May 23 19:37:57 dsteiner3 os-prober: debug: running /usr/lib/os-probes/50mounted-tests on /dev/sda2
May 23 19:37:57 dsteiner3 50mounted-tests: debug: /dev/sda2 type not recognised; skipping
May 23 19:37:57 dsteiner3 os-prober: debug: os detected by /usr/lib/os-probes/50mounted-tests
May 23 19:37:57 dsteiner3 os-prober: debug: /dev/sda5: part of software raid array
May 23 19:37:57 dsteiner3 os-prober: debug: /dev/sdb1: part of software raid array
May 23 19:37:57 dsteiner3 os-prober: debug: running /usr/lib/os-probes/50mounted-tests on /dev/sdb2
May 23 19:37:57 dsteiner3 50mounted-tests: debug: /dev/sdb2 type not recognised; skipping
May 23 19:37:57 dsteiner3 os-prober: debug: os detected by /usr/lib/os-probes/50mounted-tests
May 23 19:37:57 dsteiner3 os-prober: debug: /dev/sdb5: part of software raid array
May 23 19:40:07 dsteiner3 shutdown[29838]: shutting down for system reboot

-----------------------

/var/log/apt/term.log:

Preparing to replace grub-pc 1.99-27.1 (using .../grub-pc_2.00-14_amd64.deb) ...
Unpacking replacement grub-pc ...
Preparing to replace grub-pc-bin 1.99-27.1 (using .../grub-pc-bin_2.00-14_amd64.deb) ...
Unpacking replacement grub-pc-bin ...
Preparing to replace grub2-common 1.99-27.1 (using .../grub2-common_2.00-14_amd64.deb) ...
Unpacking replacement grub2-common ...
Preparing to replace grub-common 1.99-27.1 (using .../grub-common_2.00-14_amd64.deb) ...
Unpacking replacement grub-common ...

[...]

Setting up linux-image-3.8-2-amd64 (3.8.13-1) ...
Running depmod.
Examining /etc/kernel/postinst.d.
run-parts: executing /etc/kernel/postinst.d/dkms 3.8-2-amd64 /boot/vmlinuz-3.8-2-amd64
run-parts: executing /etc/kernel/postinst.d/initramfs-tools 3.8-2-amd64 /boot/vmlinuz-3.8-2-amd64
update-initramfs: Generating /boot/initrd.img-3.8-2-amd64
run-parts: executing /etc/kernel/postinst.d/pm-utils 3.8-2-amd64 /boot/vmlinuz-3.8-2-amd64
run-parts: executing /etc/kernel/postinst.d/zz-update-grub 3.8-2-amd64 /boot/vmlinuz-3.8-2-amd64
GRUB >= 2.00 has been unpacked but not yet configured.
grub-mkconfig will not work until the upgrade is complete.
It should run later as part of configuring the new GRUB packages.

[...]

Setting up grub-common (2.00-14) ...
Installing new version of config file /etc/grub.d/05_debian_theme ...
Installing new version of config file /etc/grub.d/00_header ...
Installing new version of config file /etc/grub.d/10_linux ...
Installing new version of config file /etc/grub.d/20_linux_xen ...
Installing new version of config file /etc/grub.d/30_os-prober ...
Installing new version of config file /etc/grub.d/41_custom ...
Setting up grub2-common (2.00-14) ...
Setting up grub-pc-bin (2.00-14) ...
Setting up grub-pc (2.00-14) ...
Installing new version of config file /etc/kernel/postinst.d/zz-update-grub ...
Installing new version of config file /etc/kernel/postrm.d/zz-update-grub ...
Undefined subroutine &conffile::abs_path called at /usr/bin/ucfq line 529, <HASH> line 8.
Installation finished. No error reported.
Generating grub.cfg ...
Found background image: .background_cache.png
Found linux image: /boot/vmlinuz-3.8-2-amd64
Found initrd image: /boot/initrd.img-3.8-2-amd64
Found linux image: /boot/vmlinuz-3.2.0-4-amd64
Found initrd image: /boot/initrd.img-3.2.0-4-amd64
done

-----------------------


Debian Release: jessie/sid
  500 unstable        ftp.at.debian.org
--- Package information. ---
Depends            (Version) | Installed
============================-+-============
debconf            (>= 0.5)  | 1.5.50
 OR debconf-2.0              |
grub-common                  | 2.00-14
grub2-common     (= 2.00-14) | 2.00-14
grub-pc-bin      (= 2.00-14) | 2.00-14
ucf                          | 3.0027


Package's Recommends field is empty.

Package's Suggests field is empty.

--- Output from package bug script ---

*********************** BEGIN /proc/mounts
/dev/mapper/vg-lv / ext4 rw,relatime,errors=remount-ro,data=ordered 0 0
/dev/md0 /boot ext4 rw,relatime,data=ordered 0 0
*********************** END /proc/mounts

*********************** BEGIN /boot/grub/device.map
(hd0)	/dev/disk/by-id/ata-HDS725050KLA360_KRVN04ZAK4XEVF
(hd1)	/dev/disk/by-id/ata-HDS725050KLA360_KRVN04ZAK4ZA6F
*********************** END /boot/grub/device.map

*********************** BEGIN /boot/grub/grub.cfg
#
# DO NOT EDIT THIS FILE
#
# It is automatically generated by grub-mkconfig using templates
# from /etc/grub.d and settings from /etc/default/grub
#

### BEGIN /etc/grub.d/00_header ###
if [ -s /grubenv ]; then
  load_env
fi
set default="0"

if [ x"" = xy ]; then
  menuentry_id_option="--id"
else
  menuentry_id_option=""
fi

export menuentry_id_option

if [ "" ]; then
  set saved_entry=""
  save_env saved_entry
  set prev_saved_entry=
  save_env prev_saved_entry
  set boot_once=true
fi

function savedefault {
  if [ -z "" ]; then
    saved_entry=""
    save_env saved_entry
  fi
}

function load_video {
  if [ x = xy ]; then
    insmod all_video
  else
    insmod efi_gop
    insmod efi_uga
    insmod ieee1275_fb
    insmod vbe
    insmod vga
    insmod video_bochs
    insmod video_cirrus
  fi
}

if [ x = xy ] ; then
   font=unicode
else
insmod part_msdos
insmod part_msdos
insmod diskfilter
insmod mdraid1x
insmod ext2
set root='mduuid/ac19a7f0bc9721663342829824ef5875'
if [ x = xy ]; then
  search --no-floppy --fs-uuid --set=root --hint='mduuid/ac19a7f0bc9721663342829824ef5875'  f86ba373-8f36-4d88-afed-5ed72ca1526d
else
  search --no-floppy --fs-uuid --set=root f86ba373-8f36-4d88-afed-5ed72ca1526d
fi
    font="/grub/unicode.pf2"
fi

if loadfont  ; then
  set gfxmode=auto
  load_video
  insmod gfxterm
  set locale_dir=/locale
  set lang=en_US
  insmod gettext
fi
terminal_output gfxterm
set timeout=5
### END /etc/grub.d/00_header ###

### BEGIN /etc/grub.d/05_debian_theme ###
insmod part_msdos
insmod part_msdos
insmod diskfilter
insmod mdraid1x
insmod ext2
set root='mduuid/ac19a7f0bc9721663342829824ef5875'
if [ x = xy ]; then
  search --no-floppy --fs-uuid --set=root --hint='mduuid/ac19a7f0bc9721663342829824ef5875'  f86ba373-8f36-4d88-afed-5ed72ca1526d
else
  search --no-floppy --fs-uuid --set=root f86ba373-8f36-4d88-afed-5ed72ca1526d
fi
insmod png
if background_image /grub/.background_cache.png; then
  set color_normal=white/black
  set color_highlight=black/white
else
  set menu_color_normal=cyan/blue
  set menu_color_highlight=white/blue
fi
### END /etc/grub.d/05_debian_theme ###

### BEGIN /etc/grub.d/10_linux ###
menuentry 'Debian GNU/Linux' --class debian --class gnu-linux --class gnu --class os  'gnulinux-simple-8dc49f0a-42e7-4752-bff5-76723aca1b2e' {
	load_video
	insmod gzio
	insmod part_msdos
	insmod part_msdos
	insmod diskfilter
	insmod mdraid1x
	insmod ext2
	set root='mduuid/ac19a7f0bc9721663342829824ef5875'
	if [ x = xy ]; then
	  search --no-floppy --fs-uuid --set=root --hint='mduuid/ac19a7f0bc9721663342829824ef5875'  f86ba373-8f36-4d88-afed-5ed72ca1526d
	else
	  search --no-floppy --fs-uuid --set=root f86ba373-8f36-4d88-afed-5ed72ca1526d
	fi
	echo	'Loading Linux 3.8-2-amd64 ...'
	linux	/vmlinuz-3.8-2-amd64 root=/dev/mapper/vg-lv ro  quiet
	echo	'Loading initial ramdisk ...'
	initrd	/initrd.img-3.8-2-amd64
}
submenu 'Advanced options for Debian GNU/Linux'  'gnulinux-advanced-8dc49f0a-42e7-4752-bff5-76723aca1b2e' {
	menuentry 'Debian GNU/Linux, with Linux 3.8-2-amd64' --class debian --class gnu-linux --class gnu --class os  'gnulinux-3.8-2-amd64-advanced-8dc49f0a-42e7-4752-bff5-76723aca1b2e' {
		load_video
		insmod gzio
		insmod part_msdos
		insmod part_msdos
		insmod diskfilter
		insmod mdraid1x
		insmod ext2
		set root='mduuid/ac19a7f0bc9721663342829824ef5875'
		if [ x = xy ]; then
		  search --no-floppy --fs-uuid --set=root --hint='mduuid/ac19a7f0bc9721663342829824ef5875'  f86ba373-8f36-4d88-afed-5ed72ca1526d
		else
		  search --no-floppy --fs-uuid --set=root f86ba373-8f36-4d88-afed-5ed72ca1526d
		fi
		echo	'Loading Linux 3.8-2-amd64 ...'
		linux	/vmlinuz-3.8-2-amd64 root=/dev/mapper/vg-lv ro  quiet
		echo	'Loading initial ramdisk ...'
		initrd	/initrd.img-3.8-2-amd64
	}
	menuentry 'Debian GNU/Linux, with Linux 3.8-2-amd64 (recovery mode)' --class debian --class gnu-linux --class gnu --class os  'gnulinux-3.8-2-amd64-recovery-8dc49f0a-42e7-4752-bff5-76723aca1b2e' {
		load_video
		insmod gzio
		insmod part_msdos
		insmod part_msdos
		insmod diskfilter
		insmod mdraid1x
		insmod ext2
		set root='mduuid/ac19a7f0bc9721663342829824ef5875'
		if [ x = xy ]; then
		  search --no-floppy --fs-uuid --set=root --hint='mduuid/ac19a7f0bc9721663342829824ef5875'  f86ba373-8f36-4d88-afed-5ed72ca1526d
		else
		  search --no-floppy --fs-uuid --set=root f86ba373-8f36-4d88-afed-5ed72ca1526d
		fi
		echo	'Loading Linux 3.8-2-amd64 ...'
		linux	/vmlinuz-3.8-2-amd64 root=/dev/mapper/vg-lv ro single
		echo	'Loading initial ramdisk ...'
		initrd	/initrd.img-3.8-2-amd64
	}
	menuentry 'Debian GNU/Linux, with Linux 3.2.0-4-amd64' --class debian --class gnu-linux --class gnu --class os  'gnulinux-3.2.0-4-amd64-advanced-8dc49f0a-42e7-4752-bff5-76723aca1b2e' {
		load_video
		insmod gzio
		insmod part_msdos
		insmod part_msdos
		insmod diskfilter
		insmod mdraid1x
		insmod ext2
		set root='mduuid/ac19a7f0bc9721663342829824ef5875'
		if [ x = xy ]; then
		  search --no-floppy --fs-uuid --set=root --hint='mduuid/ac19a7f0bc9721663342829824ef5875'  f86ba373-8f36-4d88-afed-5ed72ca1526d
		else
		  search --no-floppy --fs-uuid --set=root f86ba373-8f36-4d88-afed-5ed72ca1526d
		fi
		echo	'Loading Linux 3.2.0-4-amd64 ...'
		linux	/vmlinuz-3.2.0-4-amd64 root=/dev/mapper/vg-lv ro  quiet
		echo	'Loading initial ramdisk ...'
		initrd	/initrd.img-3.2.0-4-amd64
	}
	menuentry 'Debian GNU/Linux, with Linux 3.2.0-4-amd64 (recovery mode)' --class debian --class gnu-linux --class gnu --class os  'gnulinux-3.2.0-4-amd64-recovery-8dc49f0a-42e7-4752-bff5-76723aca1b2e' {
		load_video
		insmod gzio
		insmod part_msdos
		insmod part_msdos
		insmod diskfilter
		insmod mdraid1x
		insmod ext2
		set root='mduuid/ac19a7f0bc9721663342829824ef5875'
		if [ x = xy ]; then
		  search --no-floppy --fs-uuid --set=root --hint='mduuid/ac19a7f0bc9721663342829824ef5875'  f86ba373-8f36-4d88-afed-5ed72ca1526d
		else
		  search --no-floppy --fs-uuid --set=root f86ba373-8f36-4d88-afed-5ed72ca1526d
		fi
		echo	'Loading Linux 3.2.0-4-amd64 ...'
		linux	/vmlinuz-3.2.0-4-amd64 root=/dev/mapper/vg-lv ro single
		echo	'Loading initial ramdisk ...'
		initrd	/initrd.img-3.2.0-4-amd64
	}
}

### END /etc/grub.d/10_linux ###

### BEGIN /etc/grub.d/20_linux_xen ###

### END /etc/grub.d/20_linux_xen ###

### BEGIN /etc/grub.d/30_os-prober ###
### END /etc/grub.d/30_os-prober ###

### BEGIN /etc/grub.d/30_uefi-firmware ###
### END /etc/grub.d/30_uefi-firmware ###

### BEGIN /etc/grub.d/40_custom ###
# This file provides an easy way to add custom menu entries.  Simply type the
# menu entries you want to add after this comment.  Be careful not to change
# the 'exec tail' line above.
### END /etc/grub.d/40_custom ###

### BEGIN /etc/grub.d/41_custom ###
if [ -f  /custom.cfg ]; then
  source /custom.cfg
elif [ -z "" -a -f  /custom.cfg ]; then
  source /custom.cfg;
fi
### END /etc/grub.d/41_custom ###
*********************** END /boot/grub/grub.cfg

*********************** BEGIN /proc/mdstat
Personalities : [raid1]
md1 : active raid1 sdb5[2] sda5[1]
      487753536 blocks super 1.2 [2/2] [UU]

md0 : active raid1 sdb1[2] sda1[1]
      498368 blocks super 1.2 [2/2] [UU]

unused devices: <none>
*********************** END /proc/mdstat

Hi,

(not a grub maintainer)

I have the same issue, however it is not just after updating the
latest version, but pretty much every grub update that breaks.

The issue is in either grub failing to install to the MBR on some
drives or grub skipping that step altogether.
I have an 8 disk system, the first one is a HDD for /home, this is the
one my BIOS points to for booting. The second is an SSD with / and
/boot (same partition). the other 6 are HDDs for data and grub is
unable to install the bootloader there (not really an issue since they
aren't used for booting).
I think grub is failing on those 6 drives.
Whenever there is a grub update I need to manually execute
"grub-install /dev/sda /dev/sdd" to make the system bootable.

I forgot that last week and had to use a live image and chroot to fix it.
For some reason my system refuses to boot if I set the SSD as first
boot device in the BIOS, hence the rather unusual setup.
It appears to me that grub will fail to upgrade cleanly as soon as the
device with /boot isn't the primary drive in the system. Which is also
probably the case for your RAID1 setup.

Regards,
Steven

sudo dpkg-reconfigure grub-pc

... and configure it properly.  Presumably you switched disks at some
point in the past and didn't tell the GRUB packaging so that it could
sort this out; in general this does work if done properly.

Thanks, looks good now.
I don't recall ever seeing the screen where it asks for the disks like
that. Maybe a recent introduction? I have been tracking testing/sid
since Squeeze went into freeze, so perhaps I missed it. I never
'switched' disks in this system afaik, only added.... except maybe that
one time were I was kind of forced to replace the motherboard.

It dates back to April 2009.  The installer would have dealt with
configuring it on systems installed afresh with GRUB 2; at least some
changes in hardware will force grub-pc to display it again on upgrade,
but it is probably still possible to confuse it, certainly if the old
disks are still around but no longer used for booting.  Unfortunately
the PC architecture doesn't really make it possible to do a fully
correct job here without constantly nagging people with upgrade prompts.

Since this works after reinstalling GRUB, chances are it's just that
grub-pc's debconf questions were initially configured wrongly so it
didn't reinstall to the right places automatically.  Some investigation
might still be warranted, but I don't think it needs to be
release-critical.