Yawning/Boringshill says that we're over target. Something's brewing.
What if $Whackd timer reset was a fakeout?
Get the blackhats to deploy countermeasures, only to be psyched out with their hand exposed, whitehats countermove.
Lots of reasons for having silly riddles to solve. For one, the enemy would be expending lots of resources to examine every detail in attempt to beat anon to any potentially hidden info. Deadman's switch can be performing all sorts of functions.
Besides, a detail may only seem like a riddle because context is missing; once context is supplied the expansive truths can become clear.