In my tests i found u-u operating properly on shutdown except when the
system was started on battery, and in that case the u-u.service did not
start - thus did not stop on shutdown:

$ service unattended-upgrades status
● unattended-upgrades.service - Unattended Upgrades Shutdown
   Loaded: loaded (/lib/systemd/system/unattended-upgrades.service; enabled; 
vendor preset: enabled)
   Active: inactive (dead)
Condition: start condition failed at Fri 2018-05-25 20:18:34 UTC; 38s ago
           └─ ConditionACPower=true was not met
     Docs: man:unattended-upgrade(8)

The change to not run on battery was introduced in 0.97, right before
Artful's release.

Did you start your system on battery?

** Changed in: unattended-upgrades (Ubuntu)
       Status: New => Triaged

** Changed in: unattended-upgrades (Ubuntu)
   Importance: Undecided => Medium

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Ubuntu.
https://bugs.launchpad.net/bugs/1773033

Title:
  unattended upgrade no longer actions on shutdown

Status in unattended-upgrades package in Ubuntu:
  Triaged

Bug description:
  Ubuntu 17.10 and 18.04 do not install updates with InstallOnShutdown
  flag set.

  post-install script on 14.04 and 16.04 would set options in
  /etc/apt/apt.conf.d/50unattended-upgrades and
  /etc/apt/apt.conf.d/10periodic to install updates on shutdown of
  ubuntu desktop. This worked on 17.10 also, until an update before the
  release of 18.04. After a fresh install of 18.04, ran the post install
  script. Below is the contents of the two files, updates do not run,
  even if performing an apt update and leaving the machine up for a few
  hours to download packages in the back ground. Both the unattended-
  upgrades and unattended-upgrades-shutdown log files are empty.

  Description:  Ubuntu 18.04 LTS
  Release:      18.04

  ii  unattended-upgrades                        1.1ubuntu1
  all          automatic installation of security upgrades

  
  
----------------------/etc/apt/apt.conf.d/50unattended-upgrades----------------
  Unattended-Upgrade::Allowed-Origins {
          "${distro_id}:${distro_codename}";
          "${distro_id}:${distro_codename}-security";
          // Extended Security Maintenance; doesn't necessarily exist for
          // every release and this system may not have it installed, but if
          // available, the policy for updates is such that unattended-upgrades
          // should also install from here by default.
          "${distro_id}ESM:${distro_codename}";
          "${distro_id}:${distro_codename}-updates";
  //      "${distro_id}:${distro_codename}-proposed";
  //      "${distro_id}:${distro_codename}-backports";
          "LP-PPA-libreoffice:${distro_codename}";
          "Canonical:${distro_codename}";
  };

  Unattended-Upgrade::Package-Blacklist {
  //      "vim";
  //      "libc6";
  //      "libc6-dev";
  //      "libc6-i686";
  };

  Unattended-Upgrade::DevRelease "false";
  Unattended-Upgrade::InstallOnShutdown "true";
  Unattended-Upgrade::Remove-Unused-Dependencies "true";


  ---------/etc/apt/apt.conf.d/10periodic:----------------------
  APT::Periodic::Update-Package-Lists "1";
  APT::Periodic::Download-Upgradeable-Packages "1";
  APT::Periodic::AutocleanInterval "7";
  APT::Periodic::Unattended-Upgrade "1";

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