One of the directors of the bank I worked for presented some Whoops coupons for deposit. I had to tell him the coupons were no good since they had gone BK.
We had one of the oldest Fed charters in the country and we were merging with a state chartered bank and the day the transaction closed we redeemed over $50M in bearer bonds. After we closed for the day their auditor was counting vault cash When he saw the bonds that were ready to be mailed I picked them up and explained they were not part of vault cash but pending our deposit to our Fed account. Took me 30 minutes to explain to the dumb ass how it worked since they didn't maintain an account at the Fed. I walked out the door that night with the bonds heading to the post office.