Public bug reported:

Installation of latest systemd update in -security hangs with current
versions of unattended-upgrades in supported releases. The u-u-side fix
is tracked in LP: #1778219.

Reproduction:

rbalint@yogi:~$ lxc launch ubuntu:18.04 uu-systemd-onshutdown
Creating uu-systemd-onshutdown
Starting uu-systemd-onshutdown
rbalint@yogi:~$ lxc shell uu-systemd-onshutdown 
mesg: ttyname failed: No such device
root@uu-systemd-onshutdown:~# apt update -qq
23 packages can be upgraded. Run 'apt list --upgradable' to see them.
root@uu-systemd-onshutdown:~# echo 'Unattended-Upgrade::InstallOnShutdown 
"true";' > /etc/apt/apt.conf.d/51unattended-upgrades-on-shutdown
root@uu-systemd-onshutdown:~# apt list --upgradable
Listing... Done
apport/bionic-updates 2.20.9-0ubuntu7.5 all [upgradable from: 2.20.9-0ubuntu7.4]
gettext-base/bionic-updates,bionic-security 0.19.8.1-6ubuntu0.1 amd64 
[upgradable from: 0.19.8.1-6]
kmod/bionic-updates 24-1ubuntu3.1 amd64 [upgradable from: 24-1ubuntu3]
libglib2.0-0/bionic-updates 2.56.3-0ubuntu0.18.04.1 amd64 [upgradable from: 
2.56.2-0ubuntu0.18.04.2]
libglib2.0-data/bionic-updates 2.56.3-0ubuntu0.18.04.1 all [upgradable from: 
2.56.2-0ubuntu0.18.04.2]
libkmod2/bionic-updates 24-1ubuntu3.1 amd64 [upgradable from: 24-1ubuntu3]
libmspack0/bionic-updates,bionic-security 0.6-3ubuntu0.2 amd64 [upgradable 
from: 0.6-3ubuntu0.1]
libnss-systemd/bionic-updates,bionic-security 237-3ubuntu10.6 amd64 [upgradable 
from: 237-3ubuntu10.3]
libpam-systemd/bionic-updates,bionic-security 237-3ubuntu10.6 amd64 [upgradable 
from: 237-3ubuntu10.3]
libsystemd0/bionic-updates,bionic-security 237-3ubuntu10.6 amd64 [upgradable 
from: 237-3ubuntu10.3]
libudev1/bionic-updates,bionic-security 237-3ubuntu10.6 amd64 [upgradable from: 
237-3ubuntu10.3]
lxd/bionic-updates 3.0.2-0ubuntu1~18.04.1 amd64 [upgradable from: 
3.0.1-0ubuntu1~18.04.1]
lxd-client/bionic-updates 3.0.2-0ubuntu1~18.04.1 amd64 [upgradable from: 
3.0.1-0ubuntu1~18.04.1]
openssh-client/bionic-updates,bionic-security 1:7.6p1-4ubuntu0.1 amd64 
[upgradable from: 1:7.6p1-4]
openssh-server/bionic-updates,bionic-security 1:7.6p1-4ubuntu0.1 amd64 
[upgradable from: 1:7.6p1-4]
openssh-sftp-server/bionic-updates,bionic-security 1:7.6p1-4ubuntu0.1 amd64 
[upgradable from: 1:7.6p1-4]
python3-apport/bionic-updates 2.20.9-0ubuntu7.5 all [upgradable from: 
2.20.9-0ubuntu7.4]
python3-distupgrade/bionic-updates 1:18.04.28 all [upgradable from: 1:18.04.27]
python3-problem-report/bionic-updates 2.20.9-0ubuntu7.5 all [upgradable from: 
2.20.9-0ubuntu7.4]
systemd/bionic-updates,bionic-security 237-3ubuntu10.6 amd64 [upgradable from: 
237-3ubuntu10.3]
systemd-sysv/bionic-updates,bionic-security 237-3ubuntu10.6 amd64 [upgradable 
from: 237-3ubuntu10.3]
ubuntu-release-upgrader-core/bionic-updates 1:18.04.28 all [upgradable from: 
1:18.04.27]
udev/bionic-updates,bionic-security 237-3ubuntu10.6 amd64 [upgradable from: 
237-3ubuntu10.3]
root@uu-systemd-onshutdown:~# reboot

Session terminated, terminating shell...Terminated
root@uu-systemd-
rbalint@yogi:~$ 
rbalint@yogi:~$ lxc shell uu-systemd-onshutdown 
mesg: ttyname failed: No such device
root@uu-systemd-onshutdown:~# tail 
/var/log/unattended-upgrades/unattended-upgrades-dpkg.log
Preparing to unpack .../libsystemd0_237-3ubuntu10.6_amd64.deb ...
Unpacking libsystemd0:amd64 (237-3ubuntu10.6) over (237-3ubuntu10.3) ...
Setting up libsystemd0:amd64 (237-3ubuntu10.6) ...
Processing triggers for ureadahead (0.100.0-20) ...
Processing triggers for libc-bin (2.27-3ubuntu1) ...
Setting up systemd (237-3ubuntu10.6) ...
Failed to try-restart systemd-networkd.service: Transaction is destructive.
See system logs and 'systemctl status systemd-networkd.service' for details.
Failed to try-restart systemd-resolved.service: Transaction is destructive.
See system logs and 'systemctl status systemd-resolved.service' for details.
root@uu-systemd-onshutdown:~#  ps -ef  | cat
UID        PID  PPID  C STIME TTY          TIME CMD
root         1     0  0 15:34 ?        00:00:00 /lib/systemd/systemd --system 
--deserialize 22
root        53     1  0 15:34 ?        00:00:00 /lib/systemd/systemd-journald
systemd+   153     1  0 15:34 ?        00:00:00 /lib/systemd/systemd-networkd
systemd+   154     1  0 15:34 ?        00:00:00 /lib/systemd/systemd-resolved
message+   194     1  0 15:34 ?        00:00:00 /usr/bin/dbus-daemon --system 
--address=systemd: --nofork --nopidfile --systemd-activation --syslog-only
root       572     1  0 15:35 ?        00:00:00 /usr/bin/python3 
/usr/share/unattended-upgrades/unattended-upgrade-shutdown
root       586   572  0 15:35 ?        00:00:08 /usr/bin/python3 
/usr/bin/unattended-upgrade
root       829     0  0 15:35 ?        00:00:00 su -l
root       830   829  0 15:35 ?        00:00:00 -su
root      1244     1  0 15:35 ?        00:00:00 /lib/systemd/systemd-udevd
root      1918     1  0 15:35 ?        00:00:00 /usr/sbin/sshd -D
root      1952   586  0 15:35 ?        00:00:00 /usr/bin/python3 
/usr/bin/unattended-upgrade
root      2111  1952  0 15:35 pts/0    00:00:00 /usr/bin/dpkg --status-fd 10 
--configure --pending
root      2125  2111  0 15:35 pts/0    00:00:00 /bin/sh 
/var/lib/dpkg/info/systemd.postinst configure 237-3ubuntu10.3
root      2165  2125  0 15:35 pts/0    00:00:00 systemctl try-restart 
systemd-journald.service
root      2170     0  0 15:36 ?        00:00:00 su -l
root      2171  2170  0 15:36 ?        00:00:00 -su
root      2197  2171  0 15:36 ?        00:00:00 ps -ef
root      2198  2171  0 15:36 ?        00:00:00 cat
root@uu-systemd-onshutdown:~# systemctl list-jobs 
JOB UNIT                                 TYPE    STATE  
323 reboot.target                        start   waiting
405 basic.target                         stop    waiting
359 sysinit.target                       stop    waiting
433 cloud-init.service                   stop    waiting
422 user.slice                           stop    waiting
388 snapd.socket                         stop    waiting
428 swap.target                          stop    waiting
332 shutdown.target                      start   waiting
412 slices.target                        stop    waiting
415 systemd-networkd.service             stop    waiting
338 syslog.socket                        stop    waiting
399 acpid.socket                         stop    waiting
377 uuidd.socket                         stop    waiting
416 systemd-networkd-wait-online.service stop    waiting
373 acpid.path                           stop    waiting
432 local-fs.target                      stop    waiting
437 cryptsetup.target                    stop    waiting
341 lxd.socket                           stop    waiting
491 systemd-journald.service             restart waiting
340 sockets.target                       stop    waiting
330 var-lib-lxcfs.mount                  stop    waiting
430 cloud-init-local.service             stop    waiting
453 paths.target                         stop    waiting
402 iscsid.socket                        stop    waiting
439 local-fs-pre.target                  stop    waiting
392 dbus.socket                          stop    waiting
440 systemd-resolved.service             stop    waiting
353 systemd-ask-password-console.path    stop    waiting
324 systemd-reboot.service               start   waiting
498 systemd-journal-flush.service        restart waiting
325 final.target                         start   waiting
414 systemd-sysctl.service               stop    waiting
331 run-user-0.mount                     stop    waiting
435 network.target                       stop    waiting
457 systemd-tmpfiles-setup.service       stop    waiting
458 systemd-ask-password-wall.path       stop    waiting
329 umount.target                        start   waiting
369 unattended-upgrades.service          stop    running
434 network-pre.target                   stop    waiting
436 systemd-tmpfiles-setup-dev.service   stop    waiting
456 systemd-update-utmp.service          stop    waiting
389 apport-forward.socket                stop    waiting
497 systemd-journald-audit.socket        start   waiting

43 jobs listed.
root@uu-systemd-onshutdown:~#

** Affects: systemd (Ubuntu)
     Importance: Undecided
         Status: New

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https://bugs.launchpad.net/bugs/1803391

Title:
  Systemd update installation hangs in unattended-upgrades
  InstallOnShutdown mode

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