Another example is anti-money laundering laws. They drew a cutline at $10k cash per deposit, so of course criminals started depositing $9,999 at a time. The legislative answer was to say that avoiding the $10k limit is a new crime called "structuring". So what's the actual limit then? There isn't one, you just have to not seem too suspicious. Attempting to follow the law whilst also using a lot of cash is itself a crime.
The other fun one is the suspicious activity reports banks are required to file if a customer does something, er, suspicious. What that means isn't defined anywhere. But eventually the regulators advised that knowing SARs exist is itself suspicious, so merely asking if the bank has filed a SAR on you can trigger the filing of a SAR on you.
The intended way to follow the law is to deposit large sums of cash and report them, which is not a crime.
That seems ridiculous at first glance? I'm assuming a "cutline" here is what the maximum performance is allowed to be, and asking companies to add in a fuzzy "extra" bit there, instead of building right to the line is bizarre?