You are not alone.  Remember that contract you signed with the hospital or group?  Did it specify who would pay for the tail coverage when you part ways?  Is it their bill to pay? Yours? Split it 50-50%? If you are responsible for paying the bill, you can decide where to buy your tail.  MEDPLI helps doctors lower their tail costs by shopping the standalone tail marketplace when they change jobs. Recently, we helped an Illinois Obstetrician save $30,000 on her tail.  It pays to have a MEDPLI Insurance Broker!