Given your answer, I think this would be a good situation to use the new Whonix News functionality that you described here:
whonixcheck Whonix 14 ideas
Some advance notice should be provided before a version upgrade so users know to backup and/or expect a big update. Ideally, users should confirm the updates that they apply anyway but it’s safe to say that’s probably not the case.
WHONIX NEWS:
Whonix XX will be released on Jan 1, 2017. Please prepare your system by reading the upgrade instructions here: www…