I looked into this a bit more and 'sudo -K' and 'sudo -k' will only
remove/invalidate the timestamp on the tty/pseudo-terminal that sudo was
called from. This is a rather old change. From the upstream changelog:

338) Rewrote timestamp handling.  For the default case, a directory is used
     instead of a file.  For the tty-based case, the timestamp is just a
     file in that directory (eg. /var/run/sudo/username/tty).  You now only
     get the lecture once, even in the tty case.  The goal here is to allow
     the tty and non-tty schemes to coexist, though it is worth noting that
     when you update a tty file, the mtime of the dir gets updated too.

It would be more clear if the man page said that '-k' and '-K' removed
the user's timestamp for the tty or pseudo-terminal that sudo was run
from.

** Changed in: sudo (Ubuntu)
       Status: New => Confirmed

** Summary changed:

- sudo -K is not removing the user's timestamp entirely
+ sudo -K should remove all user's timestamps

** Changed in: sudo (Ubuntu)
   Importance: Undecided => Wishlist

-- 
sudo -K should remove all user's timestamps
https://bugs.launchpad.net/bugs/269992
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