This bug was fixed in the package ubuntu-release-upgrader - 1:19.10.15.2

---------------
ubuntu-release-upgrader (1:19.10.15.2) eoan; urgency=medium

  * Fix binary and binary-indep targets to work as intended (LP:
#1850851)

ubuntu-release-upgrader (1:19.10.15.1) eoan; urgency=medium

  * do-release-upgrade: also check for linux-image- in reboot-required.pkgs,
    refusing upgrading before a reboot is performed. (LP: #1844805)

ubuntu-release-upgrader (1:19.10.15) eoan; urgency=medium

  * Don't check for validity of /usr/bin/python symlink because this is no
    longer relevant to the upgrades (and the printed error message was
    inaccurate).  LP: #1825655.
  * Clean up remaining references to /usr/bin/python (tests and utilities)
    in the source.

ubuntu-release-upgrader (1:19.10.14) eoan; urgency=medium

  * DistUpgrade/DistUpgradeCache.py: New python3-apt bindings no longer provide
    Package.section, so switch to using Package.{candidate,installed}.section
    whenever applicable. This fixes broken partial upgrades. (LP: #1841675)

ubuntu-release-upgrader (1:19.10.13) eoan; urgency=medium

  [ Brian Murray ]
  * DistUpgrade/DistUpgradeQuirks.py: do not include gnome-system-monitor in
    the deb to snap transition anymore. (LP: #1845485)
  * DistUpgrade/DistUpgradeQuirks.py: improve wording regarding not being able
    to upgrade from a system with an apt architecture of i386.

  [ Łukasz 'sil2100' Zemczak ]
  * DistUpgrade/DistUpgradeQuirks.py: slightly refactor code to fix related
    unit tests.

 -- Adam Conrad <adcon...@ubuntu.com>  Thu, 31 Oct 2019 13:38:35 -0600

** Changed in: ubuntu-release-upgrader (Ubuntu Eoan)
       Status: Fix Committed => Fix Released

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https://bugs.launchpad.net/bugs/1844805

Title:
  virtualbox, virtualbox-dkms, virtualbox-qt fail during upgrade from
  19.04 to 19.10

Status in ubuntu-release-upgrader package in Ubuntu:
  Fix Released
Status in ubuntu-release-upgrader source package in Xenial:
  Fix Committed
Status in ubuntu-release-upgrader source package in Bionic:
  Fix Committed
Status in ubuntu-release-upgrader source package in Disco:
  Fix Committed
Status in ubuntu-release-upgrader source package in Eoan:
  Fix Released
Status in ubuntu-release-upgrader source package in Focal:
  Fix Released

Bug description:
  [Impact]

  Currently some users can encounter an error while upgrading from disco
  to eoan whenever the kernel has been upgraded before starting the
  upgrade without a reboot first. This can cause certain dkms packages
  (like virtualbox-dkms) in certain circumstances to fail. The reported
  case was that the user was running a not-up-to-date kernel, even
  though being fully upgraded but not rebooted, while only the one in
  -upgrades had fixes to support building the virtualbox dkms package.

  We need to make sure such issues do not happen again. Since such
  issues can occur, we not only have to force people to be fully up-to-
  date before starting the upgrade but also request a reboot if the
  kernel has been upgraded. This way we'll be sure the users are running
  the latest kernel.

  [Test Case]

   * On a disco system, enable {disco,eoan}-proposed and upgrade 
ubuntu-release-upgrader-core.
   * Upgrade the kernel packages
     - This can usually be done by simply installing the new kernel package 
that is currently in {disco,eoan}-proposed. Basically most of the time there's 
always a new kernel in-flight.
     - If not, another possibility is looking for a newer kernel in one of the 
proposed kernel PPAs.
   * Make sure your system is fully up-to-date.
   * Run `do-release-upgrade` and make sure it does not allow you to continue 
the upgrade without restarting the system first.

  [Regression Potential]

  I can't easily think of any regression potential, any issues in the
  changed code would most likely make the bugfix not work. The most
  absurd thing I could think of is the match being horribly wrong,
  asking users to do a reboot where it was not really necessary - but
  that's basically impossible and, actually, not a big deal.

  [Original Description]

  I upgraded this morning from 19.04 to 19.10 with `do-release-upgrade
  -d` and the upgrade reported that virtualbox, virtualbox-qt, and
  virtualbox-dkms encountered problems during the upgrade.

  I uninstalled and reinstalled them after rebooting and saw this:

  ```
  ERROR (dkms apport): kernel package linux-headers-5.0.0-29-generic is not 
supported
  Error! Bad return status for module build on kernel: 5.0.0-29-generic (x86_64)
  Consult /var/lib/dkms/virtualbox/6.0.12/build/make.log for more information.
  ```

  I think this means the version of virtualbox in 19.10 doesn't want to
  compile against a 19.04 kernel?

  The problem with this, of course, is that everyone who upgrades from
  19.04 to 19.10 is going to have a 19.04 kernel installed during the
  upgrade (and afterward, since one old kernel is saved), so the upgrade
  will fail for everyone with virtualbox installed. I think this needs
  to be fixed?

  ProblemType: Bug
  DistroRelease: Ubuntu 19.10
  Package: virtualbox (not installed)
  ProcVersionSignature: Ubuntu 5.3.0-10.11-generic 5.3.0-rc8
  Uname: Linux 5.3.0-10-generic x86_64
  ApportVersion: 2.20.11-0ubuntu7
  Architecture: amd64
  CurrentDesktop: ubuntu:GNOME
  Date: Fri Sep 20 10:47:44 2019
  InstallationDate: Installed on 2019-09-12 (7 days ago)
  InstallationMedia: Ubuntu 19.04 "Disco Dingo" - Release amd64 (20190416)
  SourcePackage: virtualbox
  UpgradeStatus: Upgraded to eoan on 2019-09-20 (0 days ago)

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