On the night of December 8, 2006, as "Picton Castle" was roughly south-east of Cape Cod, Massachusetts, the ship encountered bad weather. A wave swamped the ship, sweeping overboard crew member Laura Gainey, daughter of Bob Gainey. Gainey was not wearing a life jacket or a survival suit but was expected to be able to survive up to 36 hours due to warm water temperatures. A search for her by the "Picton Castle", aircraft of the United States and Canadian Coast Guards, and nearby merchant vessels, was unsuccessful and called off after three days, and the ship continued on its voyage.