Using my example, I did:

systemd-analyze set-log-level debug
systemctl stop cups.service
touch /var/cache/cups/org.cups.cupsd
sudo rm /var/cache/cups/org.cups.cupsd
systemctl stop cups.service
systemd-analyze set-log-level info
journalctl -b > /tmp/journal.txt

And journal.txt attached. Note that I had to do this a number of times
to reproduce the race. The last time was the time that I got "Job for
cups.service canceled.". There were one or two other occurrences that I
missed.

Interestingly, "cups.service: Start request repeated too quickly."
appears on a successful run. Where I got the "canceled" error, nothing
unusual is logged.

** Attachment added: "journal.txt"
   
https://bugs.launchpad.net/ubuntu/+source/cups/+bug/1642966/+attachment/4786403/+files/journal.txt

** Changed in: cups (Ubuntu)
       Status: Incomplete => Confirmed

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https://bugs.launchpad.net/bugs/1642966

Title:
  package cups-daemon 2.1.3-4 failed to install/upgrade: subprocess new
  pre-removal script returned error exit status 1

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