I need help. We have a very stale dated check drawn on our bank with an endorsement issue. It was deposited last month and we want to return it due to the improper endorsement. Are we still able to do this since it was stale dated? It may have no bearing but I'm just not sure.

Since you are past your midnight deadline, you will need an affidavit of forged endorsement from the payee which you send along with the copy of the check without entry to the bank of first deposit.

The only thing the UCC says about stale dated checks is that the Bank can voluntarily elect to pay stale dated checks in good faith. The bank of first deposit can't claim that you should have returned the item stale dated since they elected to accept the risk by taking the stale dated check for deposit.

Unfortunately the payee appears to have passed away. The estate apparently is trying to push the check through. They took a check payable to Joe Schmo and endorsed it Joe Schmo Estate. So, I don't believe the payee will sign an affidavit. Our customer had already provided a replacement check, which was cashed a while back. We are in Florida, so I know we have the one year on endorsement, but is there an affidavit our customer can sign given the situation?

You paid the check in good faith under UCC 4-404.

UCC 4-403 places responsibility on your customer to update their stop payment every six months. At this point your customer will have to deal direct with the executor of the estate.

This doesn't appear to be an endorsement issue, but a duplicate payment issue. But, as Brian notes above, since both payments were properly issued by your depositor and paid in good faith, the bank does not have a dog in the fight.