in 'uu' context and only during the shutdown operation seems like.

I just ran 'uu' from the CLI and it went well :

$ sudo unattended-upgrade --debug
...
Log started: 2018-11-01  19:10:16
(Reading database ... 56537 files and directories currently installed.)
Preparing to unpack .../linux-cloud-tools-common_4.15.0-36.39_all.deb ...
Unpacking linux-cloud-tools-common (4.15.0-36.39) over (4.15.0-34.37) ...
Setting up linux-cloud-tools-common (4.15.0-36.39) ...
Processing triggers for ureadahead (0.100.0-20) ...
Processing triggers for man-db (2.8.3-2ubuntu0.1) ...
left to upgrade {'libcurl4', 'curl'}
adjusting candidate version: linux-cloud-tools-common=4.15.0-36.39
applying set ['libcurl4', 'curl']
Log ended: 2018-11-01  19:10:20
...

ii  linux-cloud-tools-common            4.15.0-36.39
all          Linux kernel version specific cloud tools for version
4.15.0

During the shutdown procedure, it seems like something send a SIGTERM to
'uu' which cause the installation to not complete :

2018-11-01 14:20:26,426 INFO Writing dpkg log to 
/var/log/unattended-upgrades/unattended-upgrades-dpkg.log 
2018-11-01 14:25:23,996 WARNING SIGTERM received, will stop 
2018-11-01 14:25:24,027 WARNING SIGTERM received, will stop 
2018-11-01 14:25:24,578 ERROR Installing the upgrades failed! 
2018-11-01 14:25:24,579 ERROR error message: installArchives() failed 
2018-11-01 14:25:24,579 ERROR dpkg returned a error! See 
/var/log/unattended-upgrades/unattended-upgrades-dpkg.log for details

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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.

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