Here is a recap of my day of work :

The unattended-upgrades.service unit never runs the ExecStop because it
is not enabled as we see here :

# systemctl status unattended-upgrades.service 
● unattended-upgrades.service - Unattended Upgrades Shutdown
   Loaded: loaded (/lib/systemd/system/unattended-upgrades.service; enabled; 
vendor preset: enabled)
   Active: inactive (dead)           <<<<<<<<<<<<<<<
     Docs: man:unattended-upgrade(8)

This is caused by a missing "Default-Start" header in /etc/init.d
/unattended-upgrades. Trying to enable the unit leads to :

# systemctl enable unattended-upgrades.service
Synchronizing state of unattended-upgrades.service with SysV init with 
/lib/systemd/systemd-sysv-install...
Executing /lib/systemd/systemd-sysv-install enable unattended-upgrades
update-rc.d: error: unattended-upgrades Default-Start contains no runlevels, 
aborting.

I'm currently working on fixing all this in the packaging so we get a
correctly working unit after the upgrade of the package.

I have also reworked the unit :

[Unit]
Description=Unattended Upgrades Shutdown
DefaultDependencies=no
After=network.target local-fs.target
RequiresMountsFor=/var/log /var/run
Documentation=man:unattended-upgrade(8)

[Service]
Type=oneshot
RemainAfterExit=yes
ExecStop=/usr/share/unattended-upgrades/unattended-upgrade-shutdown
TimeoutStopSec=900

[Install]
WantedBy=multi-user.target

With this configuration, the unit runs the ExecStop as expected. I also
tested using Unattended-Upgrade::InstallOnShutdown "true" and it works
as expected, which is to block the shutdown for upgrade with the network
being available.

I should have that available for testing tomorrow.

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https://bugs.launchpad.net/bugs/1654600

Title:
  unattended-upgrade-shutdown hangs when /var is a separate filesystem

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