Note:

I suspect that issue is related to the fact that some 'package(s)'
(virtualbox in your case) are simply 'removed' (letting their settings
still active).

Myself always 'purge' the package when removing them. Virtualbox is also
install on a few machines here; and never had  apt refusing the
autoremoval. That it.

Also seen many users reporting against 'dpkg' (apport choice) most of
the time, with a title such "package xxxx failed to install, package is
already installed and configured" . I also never had such an issue; so
also suspecting old settings left behind, disturbing the autoremoval
process.

That said, "apt-get autoremove" should really 'purge' not only 'remove'
to avoid a durty system.

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https://bugs.launchpad.net/bugs/1636203

Title:
  apt-get autoremove not removing old kernels when package
  virtualbox-5.1 is installed

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