There has been some notable problems. In one of the early Bond movies, a bright red North Sea helicopter was painted drab green to resemble a Soviet helicopter. When the paint was removed, because the original paintwork on a hard working North Sea machine had various cracks and areas of mat surface, all of the cracks then contained green paint.
The aircraft had to be completely stripped down and repainted at the Production's expense. In this situation insurance companies are in a pretty good position not to pay out, as it was ignorance rather than an accident.