Gutshot, soon after Ky. started issuing CDW licenses, friend of mine there ran into a weird problem. He had the license but the next time he tried to buy a handgun locally, NICS denied it. Several years previously he had lived in Florida and gotten fined by their state wildlife cops for some sort of minor fishing violation. Paid the fine and forgot the matter.
Well, it seems that between then and the abovementioned gun purchase, Florida had retroactively made that old offense a much more serious crime. Kentucky state police didn't catch it but the Feds sure did. He had to find a KY based attorney also licensed to practice in Florida to clear that up, and she had to fly to Tallahassee and fix it in person!
What a mess.