As pitti can't reproduce it with a clean system there is a good chance
an "unrelated" package from a PPA or cruft from an earlier upgrade
confuses apt (as far as I remember PPAs are disabled on upgrade in
Ubuntu, so it can't be new "unrelated" packages at least). These bugs
are everyone’s favorite and log-staring usually doesn't work that well,
so being able to reproduce this would be very nice…

What we can try is testing with the /var/lib/dpkg/status file from
BEFORE the upgrade. Backups of this file can be found in /var/backups:
The file "dpkg.status.X.gz" (where X is a number and .gz optional if X
is 0) modified last before the upgrade would be good to have. Note
before uploading: This file includes information about ALL packages you
have (or in that case had) installed and in which version (which you
might or might not consider private/personal information, but that
applies already to most log files, too).

Assuming we would have such a file we could try on a THROWAWAY system: -o 
dir::state::status=/path/to/file -o Debug::pkgAcqArchive::NoQueue=1 -o 
Debug::pkgDpkgPM=1
(theoretically its possible to run this on a system you wanna keep, but 
theoretically there is also no problem with juggling a bunch of running 
chainsaws… until something goes wrong in practice)
The output will likely be a mile long including the exact commands apt would 
have used to call dpkg. If that exposes the wrong order we are "good".

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https://bugs.launchpad.net/bugs/1560797

Title:
  package systemd-sysv 225-1ubuntu9.1 failed to install/upgrade:
  libgcrypt20 was unconfigured

Status in apt package in Ubuntu:
  Confirmed
Status in systemd package in Ubuntu:
  Confirmed

Bug description:
  Happened during upgrade to 16.04, don't know any more details.

  ProblemType: Package
  DistroRelease: Ubuntu 16.04
  Package: systemd-sysv 225-1ubuntu9.1
  Uname: Linux 4.4.5-040405-generic x86_64
  ApportVersion: 2.20-0ubuntu3
  Architecture: amd64
  Date: Tue Mar 22 22:56:03 2016
  ErrorMessage: pre-dependency problem - not installing systemd-sysv
  InstallationDate: Installed on 2013-04-24 (1064 days ago)
  InstallationMedia: Ubuntu 13.04 "Raring Ringtail" - Release amd64 (20130423.1)
  RelatedPackageVersions:
   dpkg 1.18.4ubuntu1
   apt  1.2.7
  SourcePackage: systemd
  Title: package systemd-sysv 225-1ubuntu9.1 failed to install/upgrade: 
pre-dependency problem - not installing systemd-sysv
  UpgradeStatus: Upgraded to xenial on 2016-03-23 (0 days ago)

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