@David, of course :

- Start from an up-to-date Ubuntu Bionic :

[root@uzimysut01 ~]# lsb_release -a
No LSB modules are available.
Distributor ID: Ubuntu
Description:    Ubuntu 18.04.1 LTS
Release:        18.04
Codename:       bionic

- Downgrade linux-cloud-tools-common to version 4.15.0-34.37 :

[root@uzimysut01 ~]# apt install linux-cloud-tools-common=4.15.0-34.37
Reading package lists... Done
Building dependency tree
Reading state information... Done
The following packages will be DOWNGRADED:
  linux-cloud-tools-common
0 upgraded, 0 newly installed, 1 downgraded, 0 to remove and 0 not upgraded.
Need to get 58.3 kB of archives.
After this operation, 7,168 B disk space will be freed.
Do you want to continue? [Y/n]
Get:1 https://repos.it.sncf.fr/ubuntu-security bionic-security/main amd64 
linux-cloud-tools-common all 4.15.0-34.37 [58.3 kB]
Fetched 58.3 kB in 0s (268 kB/s)
dpkg: warning: downgrading linux-cloud-tools-common from 4.15.0-36.39 to 
4.15.0-34.37
(Reading database ... 37537 files and directories currently installed.)
Preparing to unpack .../linux-cloud-tools-common_4.15.0-34.37_all.deb ...
Unpacking linux-cloud-tools-common (4.15.0-34.37) over (4.15.0-36.39) ...
Setting up linux-cloud-tools-common (4.15.0-34.37) ...
Processing triggers for ureadahead (0.100.0-20) ...
Processing triggers for man-db (2.8.3-2) ...

- Install unattended-upgrades :

[root@uzimysut01 ~]# apt install unattended-upgrades

- Ensure unattended-upgrades is active, and that it works in "shutdown
mode" :

[root@uzimysut01 ~]# grep Unattended-Upgrade /etc/apt/apt.conf.d/20auto-upgrades
APT::Periodic::Unattended-Upgrade "1";

[root@uzimysut01 ~]# grep InstallOnShutdown 
/etc/apt/apt.conf.d/50unattended-upgrades
Unattended-Upgrade::InstallOnShutdown "true";

- [optional] If you do not want to wait 30 minutes, modify the
TimeoutStopSec :

[root@uzimysut01 ~]# systemctl edit unattended-upgrades

[Service]
TimeoutStopSec=300

- Reboot :

[root@uzimysut01 ~]# systemctl reboot

- After reboot, dpkg is in a broken state :

[root@uzimysut01 ~]# apt dist-upgrade
E: dpkg was interrupted, you must manually run 'dpkg --configure -a' to correct 
the problem.

- State of the linux-cloud-tools-common package :

iFR linux-cloud-tools-common              4.15.0-34.37
all          Linux kernel version specific cloud tools for version
4.15.0

Thanks a lot for your help.

-- 
You received this bug notification because you are a member of Kernel
Packages, which is subscribed to linux in Ubuntu.
https://bugs.launchpad.net/bugs/1796376

Title:
  Bug #1739107 fix causes linux-cloud-tools-common not to be upgradable
  with unattended-upgrades on shutdown mode

Status in linux package in Ubuntu:
  Confirmed

Bug description:
  Since the following linux-cloud-tools-common package versions :

  Xenial : 4.4.0-135.161
  Bionic : 4.15.0-34.37

  the Systemd service unit file for hv-kvp-daemon has been modified with new 
dependencies that make the package unable to be upgraded with 
unattended-upgrades on shutdown mode.
  Unattended-upgrades hangs with the linux-cloud-tools-common package during 
"Preparing to unpack". The server restarts after the unattended-upgrades 
service timeout expires.

  - Package state after reboot :

  iFR linux-cloud-tools-common              4.15.0-34.37
  all          Linux kernel version specific cloud tools for version
  4.15.0

  - Unattended-upgrades dpkg logs :

  Log started: 2018-10-05  17:59:04
  (Reading database ... 52043 files and directories currently installed.)
  Preparing to unpack .../linux-cloud-tools-common_4.15.0-36.39_all.deb ...
  Log ended: 2018-10-05  18:00:54

  - Impact :

  The current impact is very important as all security updates are
  blocked until you manually fix each server with :

  dpkg --configure -a
  apt install --only-upgrade linux-cloud-tools-common

  - Workaround/Fix :

  As a simple straightforward fix, replacing :

  Before=shutdown.target cloud-init-local.service walinuxagent.service

  with :

  Before=shutdown.target walinuxagent.service

  makes the package upgradable during shutdown.

To manage notifications about this bug go to:
https://bugs.launchpad.net/ubuntu/+source/linux/+bug/1796376/+subscriptions

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