Public bug reported:

Virtualbox 4.3 (with extension pack) was a manually installed package
from Oracle download, not the Canonical repository.    on upgrade from
14.04.5 LTS to 16.04.1 LTS, the virtualbox package failed and gave
several warnings, some of which seemed recoverable.

Current version that was installed with the 16.04.1 upgrade is 5.0.24
-dfsg-0ubuntu1.16.04.1

My expectation was that a system compatibility check would run pre-
upgrade to alert and give the option to remove any incompatible packages
and produce a file in the home directory of the files/packages that were
removed.

As it happened, the upgrade finished but said that it did not complete
properly and the system may be in an unusable/unstable state.  The
computer would not reboot cleanly and had to have a forced shutdown.  On
reboot, there were about 30 errors/system problems detected.   Once they
were all cleared, the system did reboot cleanly.

At the end, it did appear virtualbox 5.0.24 was installed properly.

ProblemType: Package
DistroRelease: Ubuntu 16.04
Package: virtualbox 5.0.24-dfsg-0ubuntu1.16.04.1
ProcVersionSignature: Ubuntu 4.4.0-34.53-generic 4.4.15
Uname: Linux 4.4.0-34-generic x86_64
NonfreeKernelModules: nvidia_uvm nvidia_modeset nvidia
ApportVersion: 2.20.1-0ubuntu2.1
Architecture: amd64
Date: Sat Aug 27 17:01:18 2016
ErrorMessage: subprocess installed post-installation script returned error exit 
status 1
InstallationDate: Installed on 2014-08-19 (739 days ago)
InstallationMedia: Ubuntu 14.04 LTS "Trusty Tahr" - Release amd64 (20140417)
RelatedPackageVersions:
 dpkg 1.18.4ubuntu1.1
 apt  1.2.12~ubuntu16.04.1
SourcePackage: virtualbox
Title: package virtualbox 5.0.24-dfsg-0ubuntu1.16.04.1 failed to 
install/upgrade: subprocess installed post-installation script returned error 
exit status 1
UpgradeStatus: Upgraded to xenial on 2016-08-27 (0 days ago)

** Affects: virtualbox (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: amd64 apport-package xenial

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https://bugs.launchpad.net/bugs/1617735

Title:
  virtualbox failed to install on upgrade from manual install
  virtualbox-4.3

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