There is no reason to feel stupid; these are complicated situations. Especially here:
"the client cashed out the investment and the retirement account. She received two checks made payable to herself,"
Because the clients get all sorts of concepts, or family members direct them to do things without taking individual circumstances into consideration. But even when this is Direct, the brokerages don't always follow what is allowed, either.
"Level Up" is a gaming function, not a real life function.