OK. I just tried to reproduce again, by 
 * launching a m1.small, and t1.micro of ami-057bcf6c in us-east-1 in each 
availability zone that was available (for me that was 'us-east-1b', 
'us-east-1c' and 'us-east-1e', but AZ names differ per account).
 * ssh in and 'apt-get update && apt-get upgrade'
 * reboot
 * ssh in again and 'apt-get dist-upgrade'
 * reboot
 * ssh in

I was unable to reproduce any failure.
However, I did see the following:
$ egrep "(/ is busy|INFO: recovery)" i-*
i-13208a6e.txt:mount: / is busy
i-13208a6e.txt:[    1.650366] EXT4-fs (xvda1): INFO: recovery required on 
readonly filesystem
i-2f208a52.txt:mount: / is busy
i-2f208a52.txt:[    1.032102] EXT4-fs (xvda1): INFO: recovery required on 
readonly filesystem
i-41208a3c.txt:mount: / is busy
i-41208a3c.txt:[    2.027800] EXT4-fs (xvda1): INFO: recovery required on 
readonly filesystem
i-45208a38.txt:mount: / is busy
i-45208a38.txt:[1379725.446288] EXT4-fs (xvda1): INFO: recovery required on 
readonly filesystem
i-f3208a8e.txt:mount: / is busy
i-f3208a8e.txt:[819720.914345] EXT4-fs (xvda1): INFO: recovery required on 
readonly filesystem
i-fd208a80.txt:mount: / is busy
i-fd208a80.txt:[304615.135311] EXT4-fs (xvda1): INFO: recovery required on 
readonly filesystem


Basically / was not unmounted cleanly on the first reboot.  I suspect that the 
issue was that automatic fsck failed in the case the reporter saw.  The 
attachment here contains all the console logs, as well as apt history from one 
of the systems.
For easy viewing, apt-history.log is below.  It would seem like one of the  
packages in the *first* list caused a busy root filesystem.


Start-Date: 2012-10-01  13:18:28
Commandline: apt-get upgrade --assume-yes -q
Upgrade: bind9-host:i386 (9.8.1.dfsg.P1-4ubuntu0.2, 9.8.1.dfsg.P1-4ubuntu0.3), 
libapt-pkg4.12:i386 (0.8.16~exp12ubuntu10.2, 0.8.16~exp12ubuntu10.3), 
dnsutils:i386 (9.8.1.dfsg.P1-4ubuntu0.2, 9.8.1.dfsg.P1-4ubuntu0.3), 
libdbus-1-3:i386 (1.4.18-1ubuntu1, 1.4.18-1ubuntu1.1), grub2-common:i386 
(1.99-21ubuntu3.1, 1.99-21ubuntu3.4), apt-transport-https:i386 
(0.8.16~exp12ubuntu10.2, 0.8.16~exp12ubuntu10.3), libdns81:i386 
(9.8.1.dfsg.P1-4ubuntu0.2, 9.8.1.dfsg.P1-4ubuntu0.3), apport:i386 
(2.0.1-0ubuntu12, 2.0.1-0ubuntu13), grub-pc:i386 (1.99-21ubuntu3.1, 
1.99-21ubuntu3.4), libisccc80:i386 (9.8.1.dfsg.P1-4ubuntu0.2, 
9.8.1.dfsg.P1-4ubuntu0.3), isc-dhcp-client:i386 (4.1.ESV-R4-0ubuntu5.2, 
4.1.ESV-R4-0ubuntu5.5), apt-utils:i386 (0.8.16~exp12ubuntu10.2, 
0.8.16~exp12ubuntu10.3), dbus:i386 (1.4.18-1ubuntu1, 1.4.18-1ubuntu1.1), 
apt:i386 (0.8.16~exp12ubuntu10.2, 0.8.16~exp12ubuntu10.3), liblwres80:i386 
(9.8.1.dfsg.P1-4ubuntu0.2, 9.8.1.dfsg.P1-4ubuntu0.3), ubuntu-keyring:i386 
(2011.11.21, 2011.11.21.1), libxml2:i386 (2.7.8.dfsg-5.1ubuntu4.1, 
2.7.8.dfsg-5.1ubuntu4.2), libbind9-80:i386 (9.8.1.dfsg.P1-4ubuntu0.2, 
9.8.1.dfsg.P1-4ubuntu0.3), python-problem-report:i386 (2.0.1-0ubuntu12, 
2.0.1-0ubuntu13), isc-dhcp-common:i386 (4.1.ESV-R4-0ubuntu5.2, 
4.1.ESV-R4-0ubuntu5.5), grub-pc-bin:i386 (1.99-21ubuntu3.1, 1.99-21ubuntu3.4), 
libisccfg82:i386 (9.8.1.dfsg.P1-4ubuntu0.2, 9.8.1.dfsg.P1-4ubuntu0.3), 
tzdata:i386 (2012e-0ubuntu0.12.04, 2012e-0ubuntu0.12.04.1), gpgv:i386 
(1.4.11-3ubuntu2, 1.4.11-3ubuntu2.1), openssl:i386 (1.0.1-4ubuntu5.3, 
1.0.1-4ubuntu5.5), resolvconf:i386 (1.63ubuntu15, 1.63ubuntu16), libgc1c2:i386 
(7.1-8build1, 7.1-8ubuntu0.12.04.1), libapt-inst1.4:i386 
(0.8.16~exp12ubuntu10.2, 0.8.16~exp12ubuntu10.3), grub-common:i386 
(1.99-21ubuntu3.1, 1.99-21ubuntu3.4), python-apport:i386 (2.0.1-0ubuntu12, 
2.0.1-0ubuntu13), libisc83:i386 (9.8.1.dfsg.P1-4ubuntu0.2, 
9.8.1.dfsg.P1-4ubuntu0.3), linux-firmware:i386 (1.79, 1.79.1), libssl1.0.0:i386 
(1.0.1-4ubuntu5.3, 1.0.1-4ubuntu5.5), gnupg:i386 (1.4.11-3ubuntu2, 
1.4.11-3ubuntu2.1)
End-Date: 2012-10-01  13:19:21

Start-Date: 2012-10-01  13:44:57
Commandline: apt-get dist-upgrade -q --assume-yes
Install: linux-image-3.2.0-31-virtual:i386 (3.2.0-31.50)
Upgrade: linux-image-virtual:i386 (3.2.0.29.31, 3.2.0.31.34), 
linux-virtual:i386 (3.2.0.29.31, 3.2.0.31.34)
End-Date: 2012-10-01  13:45:13


** Attachment added: "console logs"
   
https://bugs.launchpad.net/ubuntu/+bug/1058517/+attachment/3361814/+files/consoles.tar.gz

** Changed in: ubuntu
   Importance: Undecided => High

** Changed in: apt
       Status: New => Invalid

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https://bugs.launchpad.net/bugs/1058517

Title:
  Upon Restart after Upgrading Apt Packages SSH Keyfiles Rejected

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