@Brian Murray

I still can reproduce this issue with 0.90ubuntu0.6
$ apt-cache policy unattended-upgrades
unattended-upgrades:
  Installed: 0.90ubuntu0.6
  Candidate: 0.90ubuntu0.6

Please check full log as attached.

Here are reproduction steps:
1. sudo /usr/bin/unattended-upgrade
2. Run the following script.
#!/bin/sh
loop=1
count=0
while [ $loop -gt 0 ]
do
    count=`expr $count + 1`
    echo "loop...$count"
    if [ `grep -r -e "status half-installed linux-headers-4.4.0-78" 
/var/log/dpkg.log | wc -l` -ge 1 ]; then
        aplay /usr/share/sounds/alsa/Front_Right.wav
        sudo reboot
    fi
    sleep 1
done

** Attachment added: "dpkg.log, term.log, history,log, syslog, 
unattended-upgrades.log"
   
https://bugs.launchpad.net/oem-priority/+bug/1690980/+attachment/4881783/+files/log_0523.tar.gz

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https://bugs.launchpad.net/bugs/1690980

Title:
  No pop-up window to warn users that system should not reboot or
  shutdown while installing security updates

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