Found the problem (I think).

The /etc/cron.daily/apt script, which I believe handles the automatic
update setting, was not marked executable on either machine.

This reveals two problems:

 - /etc/cron.daily/apt lost its executable status during the do-release-upgrade 
process (I'm quite sure I didn't change the permissions on that file myself)
 - The GUI for configuring the automatic update interval should check this and 
warn you if this script is not executable!  (Or just fix it itself.)

-- 
Ubuntu does not automatically check for updates, even when set to
https://bugs.launchpad.net/bugs/390319
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