Robie, thanks for the investigations. I have looked into what the file
/var/cache/cups/org.cups.cupsd (CUPS calls it "keepalive" file) is good
for and what CUPS does with it. The file is created by the CUPS daemon
cupsd when it needs to keep running, having active jobs, being in the
course of a reload, having the web interface active or sharing printers,
otherwise the file is removed. CUPS updates presence/no presence on
start-up and shutdown of the daemon and it does exactly the same in both
cases, so it can remain present after shutdown, depending on CUPS'
configuration. CUPS never reads this file (or checks its presence),
meaning that it is purely for advising external processes.

So for me it looks like that there is a certain system service manager
(what one usually runs as PID 1 under Linux) which checks for the
presence of keepalive files and decides based on this which daemons to
kill and which to keep running.

I do not know everything about systemd. Does systemd care about
keepalive files?

The CUPS upstream *.path makes cupsd being triggered by creating the
file, but only if the file is not there already. What is this good for?

Does this *.path also take down cupsd if one removes the keepalive file
or is systemd supposed to do so? For me cupsd does not get stopped by
that.

And why does shutdown of CUPS fail after removing the keepalive file
(with "Job for cups.service canceled.")? As CUPS does not care about it,
systemd seems to depend on it. And what in the prerm script of the CUPS
Debian package deletes the keepalive file?

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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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