Hi David,
I tried reproducing this while triaging to confirm and set bug status.

In a trivial loop like:
  for i in {1..100}; do echo $i; service apache2 restart; done;
It almost always blocks it by
  Mar 31 11:09:34 xenial-tests systemd[1]: apache2.service: Start request 
repeated too quickly.
  Mar 31 11:09:34 xenial-tests systemd[1]: Failed to start LSB: Apache2 web 
server.

I also installed wsgi and some other mods to slow down start/stop, but that 
didn't help either.
(apt-get install libapache2-mod-wsgi libapache2-mod-nss libapache2-mod-scgi 
libapache2-mod-webauth libapache2-modsecurity)
Installing these slows it down, so that systemd no more complains about it 
restarting too quickly, but it doesn't trigger the issue.

Did you something more to better trigger the issue in your tests?

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https://bugs.launchpad.net/bugs/1552822

Title:
  apache2 fails to wait on stop/restart

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