@Greg:

> 500 Bad redirection (path)
> which I have not seen listed here before - is this a new issue?

Possibly. I have not seen this error before either, in relation to this
bug. Just to be sure, can you please make sure that there aren't any
font-related partial downloads in /var/lib/update-notifier/package-data-
downloads/partial/? If there are, delete them, and check that the issue
you report still happens when reinstalling ttf-mscorefonts-installer:

  $ sudo apt-get purge ttf-mscorefonts-installer
  $ sudo apt-get install ttf-mscorefonts-installer

This trick helped a previous user who was bothered by an error that
shouldn't have occurred any longer (comments 79 to 85).

If you're still stuck with the same error, your issue would possibly be
a new bug that I think would be best reported against apt (source
package for the binary package apt-transport-https), unless I'm
mistaken:

  https://launchpad.net/ubuntu/+source/apt

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https://bugs.launchpad.net/bugs/1607535

Title:
  ttf-mscorefonts-installer 3.4+nmu1ubuntu2 fails to install core fonts

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