A customer comes in with Cashier's Checks from 2017 and 2018 with both remitter and payable to himself. He requests to use those two to purchase two more Cashier's checks, one payable to himself and one payable to someone else. Can we require that he deposit them into his account first before issuing the new Cashier's Checks?

it's your bank, so that is your decision. but for a paper trail, that would certainly be my decision.

We have a few customers who do this. We deposit them and then issue a new check.

You don't have to play the game with them. Some customers have been known to do this to hide assets from creditors (sometimes a former spouse). You can stop the wheel from spinning by stopping their ability to roll part of the official check over into another official check.

I wish it were that easy. Officers are okay with it because "he's always done this" and they aren't concerned.

Make sure that one of them signs the cashier's checks then