Chapter 7 discusses the perils of doing business with illegal charter operators through the prism of insurance considerations. The chapter discusses whether insurance is an effective tool to prevent illegal charters. Insurance and brokerage are envisaged as key markets which can arguably help ensure that there is no ambiguity given to aircraft owners about how unlikely it would be for a claim to be paid out if there were an illegal flight. The chapter examines relevant case law and explains what could possibly invalidate an insurance policy. The chapter focusses on the use of the aircraft ‘for an illegal purpose,’ and the use of the aircraft ‘for any purpose other than those stated in the schedule.’