I've done reviews on this issue a few years ago before the $250K standard coverage limit took effect. Allan Roth has come out with a review of this topic
with some useful examples.
One reader who had a large CD at a bank that failed in 2008 lost interest earned because his initial deposit was at the maximum FDIC limit. However, he was fortunate that he ensured the bank properly handled the POD listings. I described his experience in my post, $400,000 of Deposits at a Failed Bank, First-Hand Experience at ANB Financial.